Adventurer Seeks Adventuress

— Three Years of Online Dating —


On August 22, 2009, I received an email that changed my life. It was a response to a personals ad I had posted on Craigslist. It’s a strange story, some of which remains mysterious. But first, let me give you a little background.

I first tried personals ads back in 1984. I was 39. Eric Berne said that 39 was the ideal age for a man, since you were still young enough for women in their twenties but old enough for women in their fifties. But I wasn’t having such an ideal time of it. From time to time I would have a brief affair, but it had been several years since I’d had a significant long-term relationship. In addition to keeping an eye out for women I might meet in my usual circles of friends and acquaintances, I spent a fair amount of time hanging out in cafés and bars or going to folk dances, etc. Every once in a while I would hook up with someone that way, but it was few and far between. Encounters rarely led to affairs, and when they did, they usually didn’t last very long.

Like many other people in the Bay Area, I had sometimes glanced at the personals ads in the weekly San Francisco Bay Guardian and wondered how well they worked. Eventually I decided I’d try it myself. After familiarizing myself with the genre, I concluded that it was important to stand out from the generic verbiage found in most of the other ads, particularly in the heading. In my first ad, I attempted to do this in an almost comically glaring manner:

Read Homer for Pleasure?
Or Stendhal? Or Murasaki? If you do and you’re a woman, 20-40, trim, skeptical, rebellious, like hiking in woods and exploring urban labyrinths, be adventurous enough to write this similar, attractive man.

I got five responses. The first one I met was a single mother in San Francisco. She was nice and I saw her a couple more times, but in reality we had almost nothing in common beyond the fact that she had once been to France and had read one of Stendhal’s novels in college.

One of the other responses, a week or so later, proved to be more interesting. Her letter and accompanying photos indicated that she was a rather offbeat conceptual artist. So when we talked on the phone I proposed to meet her on her own terrain, so to speak. I said that the next evening at a certain time I would be in a Berkeley movie theater where an old Hitchcock film was showing. I would be off to the left side, away from the main audience (it was a large theater with mostly empty seats), and she should come there and sit down next to me. She did so. During our whispered conversation I brought out a small flashlight and showed her a few of our situationist-style leaflets from the early 1970s, notably including the “Great Moments in the Void” Trading Cards, which she loved. Then we went back to my place for champagne, grass, dancing, and the beginning of a brief but fun affair. (As it happened, she was married, but their relationship was open to affairs.)

That encounter was, of course, quite untypical. Usually I met the women at a café in Berkeley or San Francisco and things proceeded much more gradually — or, in most cases, did not proceed at all after the initial meeting.

My next ad read:

Adventurer Seeks Adventuress
“An adventurer is not someone to whom adventures happen, but someone who creates adventures.” Recount yours or suggest one.

The quote was from Guy Debord, writing in Potlatch in 1954. Three ostensible adventuresses responded to that one, one of whom turned out to be a professional mercenary! That was a one-time-only meeting, needless to say, but certainly interesting.

Note that in that pre-Internet era the communication process was rather slow and tedious. An ad appeared about a week after it was submitted; responders then had to mail in their responses to the Guardian, which then forwarded them to the ad person’s P.O. box. Since the ads were expensive and thus almost always very brief, the responders usually had only a vague general idea of whom they were responding to. And since the process was so slow, most people proceeded to a phone call and then (assuming that the conversation did not reveal significant incompatibilities) to a meeting without going through any further preliminary communication. So there was more mystery and uncertainty than there is now in online dating, where much more information is more rapidly conveyed ahead of time. Thus, as in the case of the mercenary, I often ended up meeting women whom I knew almost nothing about, women whom I might not have chosen to meet if I had known more about them. Still, that was part of the adventure!

A couple more ads on related themes:

Exploress Wanted
To explore possibilities of life hidden under the glib veneer of the 80s. Audacity essential. Send résumé (previous expeditions, present quests) to . . .

Theseus Seeks Ariadne.
To explore urban labyrinths & each other.

The latter one elicited a response with a thread enclosed in the same envelope. (If you aren’t familiar with classical mythology, do a Google search for “Theseus + Ariadne + thread”.) She turned out to be an attractive professional nude dancer who painted Jungian-style pictures and was fond of Lawrence Durrell and Anaïs Nin. So far, so good. Unfortunately, she also believed in astrology and reincarnation and claimed to remember some of her past lives. I told her that I was very skeptical about such things. We agreed to disagree about them and focus our relationship on other areas. . . .

Chinese Landscape Painting —
a hint of life’s possibilities. Join me for a stroll, Mademoiselle?

That one got only one response, but a very nice one from a bright, petite nurse, whom I saw again several times. But we eventually discontinued, in part because she was interested in having kids and I wasn’t.

For a little fun and variety, I wrote a takeoff on the generic personals style:

Insincere Man,
ignorant, insensitive, destitute, repugnant, reactionary, with no sense of humor, seeks fat ugly women for uncaring relationships.

That one always got a number of amused responses whenever I ran it (none of them fat or ugly), including a Belgian photographer who remains a friend to this day.

In some of my later ads I resumed my initial focus on classic literature. For example:

Seek Well-Read Woman
If you are one of the happy few who read authors like Basho, Herodotus, Lao Tzu, Montaigne, Euripides, Thoreau . . . tell me more.

In this one I was starting to focus a little more on myself, attempting to convey the unusual range and variety of my interests:

I love Chinese landscape painting and California landscape exploring, Appalachian tunes and French café songs, classic literature and modern adventure. Would I love you?

That one was still a bit lyrical, but I gradually reworked it into a more straightforward enumeration:

Mischievous man of letters,
French translator, folk musician, tennis player, rock climber, skeptical Zen Buddhist and mild-mannered enemy of the state seeks literate, magnanimous, venturesome and intellectually alive companion to explore the tragicomedies of life.

I ended up using variants on that latter ad most of the time, except for occasionally rerunning the “Insincere Man” one.

Incidentally, my experience was that the advantage was overwhelmingly with the advertiser. In the rare cases when I answered someone else’s ad, I almost never even received a reply. Presumably they were getting lots of other responses and I was being drowned out by the competition; whereas the women responding to my ad had gone to some trouble to communicate specifically with me (even if they may have also responded to a few others). Also, my response to an ad was going only to that one person, whereas my ad was potentially being read by hundreds or even thousands of people. So I almost always focused on doing my own ads rather than responding to others’.

As often seems to happen when you take the initiative to put yourself out there, there was a certain amount of serendipity. One responder turned out to be the ex-girlfriend of one of my cousins (I hadn’t seen her in years, but we saw each other regularly for a while and have been in touch on and off ever since that time). Others included a Japanese yoga teacher whom I’d seen at Zen retreats and a well-known folk musician whom I had seen numerous times at the Freight & Salvage and other local venues. Another was a professional writer who was researching an article about personals ads.

The most unusual interaction was in 1993 with a woman who was married to a physically disabled man. She was loyally taking care of him, but pretty stressed out and frustrated and hoped to find an amorous relation on the side. I didn’t respond because I didn’t want to get involved in that sort of scene. But she built up an intense fantasy about me and continued to write impassioned letters to my P.O. box, even addressing me with an invented name (since she didn’t know my real one). This went on for over a month. Eventually I agreed to meet her, but I saw her only that one time. She seemed like a very nice person and I felt for her, but I didn’t want to get involved in such a problematic situation.

The Guardian ads were rather expensive. Three or four lines cost around $30 (equivalent to $60 today), so I had to keep them short and didn’t run one every week. In fact, I often let it slide for months at a time. In 1990 I shifted to the East Bay Express when that paper started hosting them. The Express ads were free, so I reran them there much more regularly and met a somewhat larger number of women.

All told, during the period from 1984 to 1996 I met around ninety women by way of these ads. I was surprised to discover there were so many, but then realized that it actually amounted to less than one encounter per month. I keep a diary, so I’ve been able to review them all in the process of writing this text. I still remember some of them pretty well, but others are now just names, with the dates I met them and a sentence or two about them or what we talked about. Most of the encounters were reasonably pleasant and interesting, but the whole twelve years of ads resulted in only a few brief affairs and no enduring relationships. In 1997 I stopped doing them, and gave them little thought over the next several years.

In January 2008 I was talking with one of my Zen friends about relationships and he mentioned that he had met his wife through a personals ad. I had not been aware of this, though I have since discovered that several other couples I know met the same way. In any case, his remark served to remind me of my earlier ventures. I was vaguely aware that people now did the same sort of thing online at Craigslist. I went there and it turned out to be very easy — somewhat like the old Guardian/Express ads, but it was free and much more convenient (no need to mail in your ad or set up a P.O. box, etc.). Within a few minutes I had posted my first ad, which was similar to the one I had ended up using regularly in the Express:

Mild-mannered enemy of the state . . .
Reader with classical tastes, writer of subversive provocations, French translator, folk musician, tennis player, Zen practitioner and mild-mannered enemy of the state seeks magnanimous and intellectually alive companion to explore the tragicomedies of life.

The Craigslist setup already indicated that I was a man seeking a woman for a long-term relationship, lived in Berkeley, and was 63 years old, so I didn’t need to specify any of that in the ad itself.

Anyone can go to Craigslist (hereafter: “CL”) and browse among the thousands of personals ads from around the world, narrowing the field by indicating the geographical area, age range, and type of relationship they’re looking for. When they find an ad that appeals to them, they can send an email to that person.

One of the first responses I received was from Susan, a pleasant and intelligent woman who worked as a research scientist. We met at a café and had a nice chat for an hour or two. I felt that we had somewhat different interests and lifestyles and did not take any initiative in pursuing a relationship, but we have kept in touch and still occasionally see each other for lunch or at classical music concerts.

I continued renewing the same ad, with minor variations, and continued to receive a small but steady trickle of responses, averaging perhaps one or two per week. (Not counting the larger quantity of spam messages, often including a sexy photo, that are presumably from prostitutes and probably sent automatically to every male CL personals poster: “Hi, you sound like the guy for me! I’m 23 and have a nice body . . .”)

The legitimate responders usually picked up on one or two areas mentioned in my ad that they shared, saying that they, too, liked folk music, or knew French, or did some form of meditation, etc. If their response was pretty minimal, I would usually reply something like: “Thanks for your message. You can find out more about me (probably much more than you wish to know at this point!) at http://www.bopsecrets.org/PS/autobio.htm. I have also attached a photo. Perhaps you can do the same and tell me a bit more about yourself?”

Some of my friends have felt that a whole autobiography is a bit much to lay on someone who is just getting to know you, and I can certainly see their point. Nevertheless, having tried it both ways, I’m not convinced that giving an immediate link to the autobiography is a bad idea. In addition to conveying a lot of things about me, it also serves as a good filter: women who would be put off by it (thinking it too radical, too intellectual, too heavy, too pretentious, or whatever) would probably not be a likely match for me anyway. My writings are an integral expression of my life, not just a hobby that can be neatly separated from the “real me.” Moreover, some of my previous relationships began precisely because a woman liked them so much that she wanted to meet me. I think I’m more likely to find someone compatible that way rather than worrying about scaring off those who see such writings as a weird, regrettable liability.

Anyway, as I said, I continually renewed my ad and continued to receive occasional responses. Many of these fizzled out right away: either I was not interested enough to reply to them or they did not get back to me after my reply. (Note that online dating has a rather minimalist etiquette. Since the people involved are usually communicating with many contacts, it is not considered rude to simply cease communicating without necessarily adding any apology or justification. Sometimes people will politely sign off: “You seem like an interesting person, but I don’t think we would be a good match,” but the same message is implied even if they say nothing.) In other cases there was more extensive correspondence or perhaps a phone call, and this sometimes led to a rendezvous at a local café.

Among the interesting array of women I met during my first year and a half on CL were a radical lawyer, a real estate agent, two or three teachers, a psychologist, a psychotherapist, a marriage and family therapist, an acupuncturist, a tai chi teacher, a French translator, a Santa Cruz kayaker, a German practitioner of “aquatic massage,” and a Latvian law student who had previously managed several casinos in Europe. All of them were quite nice, but with two or three exceptions I was not inspired to follow up the encounter.

Then, on August 22, 2009, I got by far the most promising response I had received:

[Subject line: “Wonderful ad!”]

Hello Fellow Subversive,
       I read only good literature and relish it like Belgian chocolate, former social activist who is still committed to social justice, speak French, lived in France, love folk music and the good people who play it, don’t play tennis, but am very fit and active, a very deep Theravadan practitioner who reaches often for Maha- and Vajrayana influence, very intellectually oriented, but also very physical, affectionate, and sexual, and am already immensely enjoying the tragicomedic adventure of human life.
       I am [occupation, location, age and physical description omitted]. Magnanimous to a fault. I would love to find a mature, grounded, very intelligent, tender, strong, and fierce companion committed to the dharma and the beauty of life — if such a one exists.

I don’t know what you will think of that message, but I was bowled over by it. Not just because it indicated that we shared a lot of tastes and experiences, promising though that was, but because of the exquisite manner in which she expressed herself. She didn’t just say that she liked my ad, she virtually embraced it, responding to every single word, then offering her own equally concise self-description. I also liked her upbeat spirit. Most radical people are (understandably) very glum about the many problems in the world, but she did not let this prevent her from focusing as far as possible on the beauties of life and “immensely enjoying” its tragicomedies. Not only did she seem like she might be the woman I had been looking for for so long, she seemed to feel that I might be the man she had been looking for. Assuming, as she wisely cautioned herself, that “such a one exists” — a marvelously subtle final touch.

The only thing that made me a little uneasy was the fact that she was more than fifteen years younger than I. But she knew that when she responded. If she wasn’t bothered by it, neither was I.

I was quite aware that there were still a lot of unknowns. I had not met her or talked with her. I did not even know what she looked like. Nevertheless, even sight unseen, I would have traveled a long way to meet such a woman.

But I didn’t need to do anything so extreme — she was right here in the Bay Area! And her apparent enthusiasm seemed to indicate that we would definitely meet very soon. We already seemed to be so in tune with each other that I assumed that any further messages would be primarily just to arrange the details of a rendezvous. In fact, I was so excited that my first thought was to take it easy, play it cool and not do anything unusual. So I sent her an only slightly modified version of my usual generic reply:

Thanks for your nice response. I’d be happy to meet you sometime. Meanwhile, you can find out more about me at http://www.bopsecrets.org/PS/autobio.htm. I’ve also attached a photo. Perhaps you could do the same and tell me a bit more about yourself?

That type of response may have been appropriate in the cases when someone had just written me a short message saying that they liked my ad and would like to know more about me. But in this case I realized almost as soon as I hit the “Send” button that I wasn’t doing justice to her message. She had responded very attentively and creatively to my ad and I had just sent her a generic-sounding reply.

But for the moment I didn’t worry about it. Considering the affinities we seemed to share, I assumed that she would probably overlook any momentary lameness on my part.

Three days went by with no word from her. I sent another brief note asking if she had received my message. Still no response. I started to worry that I had put her off in some way.

The more I thought about it, the sicker I became. Here was probably the most promising relationship possibility I’d had in decades, and I might have blown it in a moment of thoughtlessness. After four or five days I could scarcely sleep. I would get maybe a couple hours of sleep, then lie awake mulling over how I should have responded differently, agonizing over the fact that I could not go back in time and change whatever might have caused the problem. Sometimes I got up in the middle of the night and tried doing zazen (Zen meditation) for an hour or two. It did no good — I simply could not stop myself from mentally writhing over the same fears and regrets and “if onlys”. During my waking hours I had no appetite. This continued for several days, eating almost nothing, never getting more than two or three hours of sleep, then tossing and turning the rest of the night. I don’t know how I managed to function — just on nervous energy, I guess.

I knew, of course, that objectively speaking I was no worse off than I was before: a very fortunate person by most standards, with lots of dear friends, engaged in a variety of interesting and fulfilling activities, living modestly but comfortably in the region I love. It was not as if there had actually been some terrible change in my life, like losing a loved one or undergoing a terrible accident or illness.

I knew all that, but it did not make the anguish any less acute. Usually I’m grounded enough not to dwell too much on ideal fantasies. In my previous encounters I had had occasional disappointments, but my expectations had been minimal so I wasn’t all that upset. But now suddenly, totally unexpectedly, this woman had appeared out of nowhere, seeming almost too good to be true. There seemed to be a really good chance that she was the woman I’d been looking for for such a long time. The prospect of losing her was like having a glimpse of a heavenly land of marvelous colors and then being thrown back into a drab region of nothing but black and gray.

On Day 7, after another short follow-up message had failed to elicit any response from her, I drafted a longer one trying to convey a little more fully why I had been so excited to hear from her. Then I called my friend Lora, told her the whole story and read her the draft. She encouraged me to send it: “If she doesn’t go for that, there’s something wrong with her!” So I went ahead and sent it. It read, in part:

. . . I have lots of dear friends in the different areas mentioned in my ad — political, Buddhist, musical, literary, etc. But I’m looking for a monogamous and hopefully lifelong romantic companion to share experiences in all those areas, as well as whatever else life may bring. I’ve met a number of women over the last few years, including some via Craigslist, mostly quite nice people, but none of them have really struck a chord. Usually we share one or two things but are divergent in others — one is into Zen but is indifferent about social issues; another is radical but is unaware of the joys of great literature, etc. That can be fine for a friendship centered around the particular shared activity, but for me it’s a strain trying to have an intimate relationship when there are big areas of mutual incomprehension.
       Then I received your wonderful message, which not only indicated that we share a lot of things, but which was beautifully composed in a way that suggested a really lively, wonderful woman. I thought: “There’s a really good chance that this is who I’ve been looking for!” And then, still blissed out thinking about that possibility, I typed out a few lines and hit the Send button before I realized how obnoxious it might seem.
       I hope all this doesn’t sound too depressing, like I’m some basket case. I’m usually a very sane and equanimous and cheery and fun guy, honest! But I’ve been just crushed over the last few days thinking how I may have blown this wonderful chance due to a few seconds’ thoughtlessness.
       If that indeed was the reason for your nonresponse, please forgive me. And let’s start afresh. I really want to get to know you, even if only as a friend.

On the off chance that my messages were getting lost in cyberspace or deflected into her spam box, I sent the same message from another computer and also posted a message to her on Craigslist.

Next day, still no response. I go to a party, hoping that it will take my mind off her. No such luck. I ask the host if I can use his computer, just in case she has responded since I’ve left my home. There’s a huge spread of the sort of good food I usually devour with relish, but I just nibble a few grapes and drive home. . . .

By a wicked irony, on Day 9 I had been scheduled to give a talk at Berkeley Zen Center. I went there, took my place at the front seat of the zendo, and said that instead of the talk I had planned to give I was going to talk about something else, namely a situation in which my reactions had been totally lacking in the equanimity that is usually associated with Buddhism. I then recounted the whole story up to that point, reading my ad, her response and all my subsequent messages, describing my initial elation, my growing anxiety, my sleeplessness, etc. I confessed that I was a total nervous wreck and that zazen hadn’t helped at all. I said that at the moment I felt better because it was a relief to talk to others about her, but that the anguish would probably reappear as soon as I went home. (Which it did.)

The responses were very sympathetic. Some praised my “courage” in baring myself and exposing my vulnerability in this way. (Actually, it was more a matter of desperation and inability to talk about anything else!) Others offered various suggestions. One or two wondered if her message could have been a sadistic hoax designed to arouse and then frustrate the recipient.

Anyway, the net result was that I was brought much closer to many of the people there, some of whom I had practiced with for ten or twenty years but had never previously gotten to know on such an intimate personal level. I now had lots of new allies! A small consolation, but a consolation nonetheless. It gave me the idea that in the worst case scenario I could try to turn some of the despair-energy to enriching my previous relationships and opening myself up to new ones.

That night, once again sleeplessly mulling over for the thousandth time how I should have responded to her, I decided that I would send her the sort of response I should have sent her originally — better late than never! I got up at 3:00 a.m. and worked on it for two or three hours, then went back to bed and for a change got a little more sleep. The next day I finished it and sent it. After that I felt a little more calm. I thought, “I’ve now done all I can do. If she’s still put off, a relationship probably never would have developed anyway.”

The next day (September 2) her second message arrived:

Hi Ken,
       Thank you for all your very attentive messages.
       I actually just got home from a weeklong women’s camping meditation retreat on the southwest flank of Mt Tam. It was really wonderful. I woke up crying the first morning as I realized how absolutely necessary it is for me to get out of the city every few months and find dirt and trees to live upon for several days. I haven’t been backpacking in two years. The city is so harsh and the work I do very draining. I have re-committed to taking better care. I would love to hear more about your Zen backpacking trips.
       Anyway, busily preparing for and being on the retreat is partly why you haven’t heard back from me. And yes, I was a little discouraged by your initial response and daunted by your website info. I’ve been on-line dating for a month and a half so far. It’s a lot of work — it turns out.
       I would love to meet you. Let me get myself situated and reoriented from my trip — I’ll email you in a week or so and we can figure out a time if you’re still available — if that’s okay with you.

Imagine my relief! It was as if I had suddenly been plucked out of hell and wafted up to Cloud Nine! Not only did her Mt. Tamalpais retreat explain the long delay, but her message seemed to indicate that she was as enthusiastic as ever about meeting me, and that there were no significant problems. Or at least she was tactful enough to make it seem like there weren’t — she thanked me for all of my “very attentive” messages (when she might have been freaked out by their quantity and intensity) while gently characterizing my first message as “a little discouraging” (when she might justifiably have said “disappointing” or “inadequate”).

The only slight downside was that I would still have to wait “a week or so” to meet her. Quite understandable — coming back from her retreat I could imagine that she might have a bunch of things to catch up with — but the suspense was still nerve-wracking.

Meanwhile, I deleted my current Craigslist ad, canceled a date and discontinued correspondence with some other CL contacts, telling them that until further notice I had no interest in anyone but this new woman.

The next day I happily spent a large part of the afternoon hunting up some Belgian chocolate to bring her. I had to go to several different stores because, as I explained to the puzzled store clerks, it had to be from Belgium — chocolate from anywhere else would not do!

A couple days later she sent two photos of herself. This resolved the interesting question as to how I would react if she had turned out to be really homely. Given my strong predispositions toward her in so many other regards, I think I could have tolerated much more homeliness than I usually would, but still . . . Fortunately, she turned out to be quite attractive, so that was a nonissue. In addition, the light, cheery tone of her accompanying message gave me a stronger impression that there were no problems, that we were already on relaxed, friendly terms. So I was pretty happy and optimistic, even if nervously so. I still wasn’t getting much sleep, but now it was due to excitement rather than despair!

A two-day Zen sesshin (intensive meditation retreat) offered a welcome period of grounding, or at least distraction, while I was waiting.

A couple days after that, I sent her a brief query to see how her schedule was looking. No response. As more days went by with no word from her, I nervously asked myself whether “a week or so” meant “about a week” or “a little more than a week” or perhaps “a week or two.”

The most likely reason I could think of for the delay was that she had had some previous engagements with other online dating contacts. Maybe she had met someone interesting and wanted to see how that panned out before getting back to me. Or perhaps she had had second thoughts about the age difference. Another possibility, horrible to imagine, was that I had once again managed to put her off in some way. But unlike the earlier delay, where the lameness of my first reply was pretty clear to me, I couldn’t see anything in my later messages that was all that egregious, unless she had been turned off by my evident eagerness to meet her.

After another week had gone by, I wrote a longer message, hoping to elicit a response from her one way or the other. I tried to keep it chatty and upbeat, but if that message, or any of my earlier ones, seemed a bit frantic or obsessive, I was hoping that she would try to put herself in my place, that she would see how the peculiar sequence of events had thrown me onto an emotional roller coaster — a tantalizing vision dangled before me, followed by a mysterious week-long silence, followed by a renewed and seemingly even more justified hope, followed by two weeks of suspense and then increasing foreboding.

Three more days went by, and then I got this message (September 18):

Hi Ken,
I’m sorry to leave you hanging for so long. I have realized I am not ready to get involved right now. I wish you well and much luck in finding your love. Take care.

I still don’t understand what really happened. When I looked back just two weeks earlier (“I would love to meet you”) and considered the enthusiasm of her original message just a week before that, I was puzzled. Especially since I had said that I was quite willing to meet her simply as a possible friend if she did not think a romantic relation was likely. I could understand that she might have gotten OD’d with online dating and want to step back and take a break from it. But her message sounded more like a final farewell than a temporary postponement.

About the only good thing was that at least the suspense was over. I wasn’t sure what I was going to do next, but it seemed clear that there was no point in mulling over further messages to her.

(Incidentally, for those who may wonder if this was all some elaborate practical joke: I had done a little Internet detective work and found out her full name. I had no intention of stalking her or otherwise bothering her, but I had verified that she was indeed a real person. In order to protect her privacy, in the present text I have suppressed her first name, occupation, location, age and physical self-description. It was by putting some of those things together that I was able to discover her identity. From this point on I will refer to her as “Monelle.”)

My first reaction was to try to turn the energy I had directed toward her to other women. I immediately reposted my ad on CL. But one of my friends reminded me that there were also lots of other online dating sites. This was a real lifesaver. I had been vaguely aware that such sites existed, but had not looked into them since CL seemed so easy. My impression was that online dating services were very complicated and expensive. There are such companies, but actually the various sites that my friend recommended were not all that complicated or expensive, and in fact some of them were free. Over the next few days I signed up at five different ones.

The first one, which I still like best, was OkCupid. The others were Match.com, Chemistry.com, eHarmony, and Plenty of Fish.

Plenty of Fish is free, but it’s so ugly and poorly organized that I almost never bother to go there. Chemistry.com and eHarmony are a bit pricy ($30-$50 per month) and both have a rather annoying interface: you must wait for the site to present you with a small number of suggested matches supposedly selected for likely compatibility. In my experience, this supposedly scientifically verified compatibility doesn’t amount to much. I have maintained my membership in both of them because I have occasionally met someone interesting through them, but I have been much more satisfied with the two sites that enable more flexible interaction with the vast numbers of other members: OkCupid and Match.com.

For simplicity’s sake, I’m going to describe how OkCupid works. Match.com is pretty similar. (OkCupid is also free, whereas Match.com costs around $25 per month.)

When I first went to OkCupid (hereafter: “OKC”), I signed in, chose a pseudonym (my “user name”), answered a few routine questions (age, ethnicity, height, body type, education, occupation, religion, city of residence), uploaded a few photos, then took some time to compose the rest of my “profile.”

Your profile is a webpage that can include pretty much anything you want to put in it to describe yourself and the type of person you’re looking for. It’s an interesting challenge in self-definition and self-presentation. OKC facilitates the process by presenting a series of boxes to fill in, from “What I’m doing with my life” to “Favorite books, movies, shows, music, and food.” You can also specify whether or not you have children, what languages you know, whether you smoke, drink, or take drugs, etc. You are also encouraged, though not required, to answer a number of questions on all sorts of topics, which may help give a general idea of your personal tastes and social and political views. While such profiles have their limits, they enable people to give a fairly extensive impression of what kind of people they are.

By way of example, here’s my current OKC profile. Although I occasionally tweak it, it’s still mostly the same as my original version.

After completing my profile, I spent the next couple days exploring the site, learning the various ways of navigating it and browsing the profiles of women who were within my tentative age and geographical range. I soon came across someone familiar, a woman whom I’d seen at a couple of Zen sesshins but never spoken to. I popped her a message. She replied that she had recently met a guy through OKC and was on the verge of closing her profile since the new relationship seemed to be working well. (Over a year later it still is.)

I spent much of the next day with my friend Kayla, with whom I used to do proofreading work. She had had a lot of experience with online dating, and a few months earlier had composed and performed an entertaining and moving one-person drama in which she narrated some of her experiences. We discussed my recent adventure, speculating about what might have caused Monelle to change her mind (she thought I might have scared her off by coming on too strong). She also pointed out some limitations in my manner of relating to people, at least as she had perceived it in our encounters over the years. She felt that although I was politely attentive, I often failed to fully enter into the other person’s concerns so as to develop a real conversational give-and-take. She granted that this is a common failing among men, whereas women tend to enter more naturally into such interactions; but she mentioned one of our mutual male friends with whom she had a very good ongoing connection of this kind. To her relief, I was very receptive to her criticisms. I had decided that I might as well put this trauma to positive use by using it as a point of departure to focus on reevaluating all aspects of my relationships (not only amorous ones). Kayla also pointed out that my all-or-nothing attitude meant that I had missed out on a lot of potentially rich relations with women whom I wrote off when it became evident that they weren’t “the one.” And then in the rare cases where the “ultimate” relationship seemed possible, such as with Monelle, I was naturally more nervous and more easily became ungrounded. I completely agreed with that point. In fact, I had already decided to try to cultivate more “intermediary” relations — getting on fairly intimate-friendly terms with a greater variety of women without worrying so much about whether they might be a potential lover or partner.

(This conversation took place while we were driving to Fremont to see an exhibit of photographs by my friend Camille — the Belgian woman whom I had met nearly twenty years earlier through an East Bay Express ad.)

When I got back home that evening and was once again browsing OKC, I got into an instant messaging conversation with a San Francisco woman. Judging from her profile, I doubted that we would be a likely long-term match, but she had specified that she was interested in short-term as well as long-term dating. She was also quite pretty and among other things mentioned that she enjoyed exploring the back ways of San Francisco. I met her a few days later in the city. We hit it off pretty well and for our next rendezvous arranged to explore some of the “hidden stairways” in the North Beach area. A few days after that she came over to Berkeley to do some explorations on this side of the Bay. Soon afterwards, however, we agreed that we were not a very good match.

The ending of the above paragraph may seem rather unsatisfying. You perhaps would like to know more details about what we did or did not do together, or what caused us to discontinue. But I’m going to be fairly discreet about all these encounters. First of all, one of the reasons I’ve been able to work up the nerve to make this text public is that I have reassured myself that I don’t need to reveal everything. Second, and much more important, I don’t want to disturb others’ privacy. Even though I have used pseudonyms for all of the women I’ve met, in a few cases it might still be possible for someone to figure out who one or another of them is. And in any case, the women themselves will be seeing this text — I’m still in email touch with virtually all of them and have let them all know about it.

I think you can see that it would be very ticklish to go into much detail, particularly in that great majority of cases when we did not see each other again after a first meeting. Did we mutually agree that we were not a match? Or was one person attracted but the other didn’t reciprocate? In a few cases I will describe others’ rejection of me, but I think it would be discourteous to specify the instances when I decided not to follow up an encounter, let alone to go into my reasons. Suffice it to say that an intimate relationship with anyone is always a long shot. There are countless ways that people can fail to click, whether because of differences of backgrounds or tastes or viewpoints, or because of lack of “chemistry.” Although that latter term is often used as a euphemism for physical attraction, it also includes all sorts of compatibilities or incompatibilities of personalities, temperaments, mannerisms, moods, rhythms, senses of humor, whether you feel in tune with each other, or excited with each other, or comfortable with each other. In addition to more “objective” factors such as geographical distance or different family or occupational priorities.

I want to stress that virtually all of the women I’ve met through online dating have been wonderful people. I’m not saying that just to be nice. Bear in mind that I filtered out far more women than I met. The ones I decided to meet were those who seemed particularly interesting, so it’s not surprising that they usually turned out to be so. The extremely brief and fragmentary descriptions of them in this text do not begin to do them justice, but are simply intended to situate them and give a little idea of their diversity. (My original draft had quite a few more personal touches and anecdotes, but in some cases the women involved requested that I delete them because they might make them too recognizable.)

From here on I’m going to note each of my online dating encounters as it occurs. I won’t mention the women I only communicated with via phone or email unless there is some particular point of interest. Unless otherwise indicated, the meetings took place at some café in Berkeley.

Needless to say, during all this time I was continuing many other activities — working, reading, writing, translating, corresponding, hiking, tennis, Zen retreats, discussion groups, folk music gatherings, etc. But I won’t mention them except when they have some bearing on this venture. (If you’re wondering how I have the time for all these things, I do freelance translating and editing work at home and my schedule is very flexible.)

September 22, 2009. Met Rebecca (CL), a sculptor and long-time student of the Tibetan Buddhist teacher Chogyam Trungpa.

September 25. Long phone talk with my friend Liz in Colorado. She was my first real crush, back in the 1950s when I was in sixth grade and she was in fifth. I reconnected with her in the 1980s and she has since been one of my closest friends. We see each other all too rarely, but every few months we have a long phone talk and enjoy catching up with each other’s lives. In this case, the lion’s share was of course my story about Monelle and the beginning of my subsequent adventures in online dating.

September 27. Attended an all-day workshop on “Awakened Relationships.” I’m usually not much into that sort of thing, but in this case it seemed so timely and so relevant to my current situation that I thought I would be foolish to pass it up. It was led by two women who combined therapist backgrounds with a “Nondualist” spiritual practice. They discussed some of the dynamics of relationships and also had us act out different kinds of interactions with each other. I found it quite interesting and worthwhile.

September 28. Dinner with Virginia, a young woman whom I had seen at Berkeley Zen Center but never talked to. The day after my BZC talk about Monelle she had sent me a sympathetic email, and we decided to get together to get to know each other. The age difference (she’s in her 30s) pretty much nixed any fleeting fantasies I might have had about a romantic relationship, but the way we had met nevertheless lent a certain emotional intimacy to our connection. I saw her again several times over the next few months and appreciated her feedback regarding my online dating adventures.

September 29. Met Barbara (CL), who works for various social justice-related NGOs.

October 1. Met Jill (OKC), a psychologist who works in community mental health. I had previously seen her at some local folk music gatherings.

October 2. Met Natalie (OKC), a Vipassana practitioner who had lived in Greece and France. She seemed quite congenial and I suggested seeing each other again. She said okay, but on the understanding that it would be only for friendship. A few days later she emailed me suggesting that we get together again. I begged off for the moment because by that time I had become involved in several other potentially romantic connections. In retrospect, this was foolish. Very possibly she had changed her mind and was thinking that maybe a romantic relationship was possible after all, or perhaps she hadn’t even intended to seem so negative in the first place. In any case, soon afterwards I noticed that she had removed her OKC profile and when I asked her about that, she said she’d met someone else. (Over a year later, when I was getting her feedback regarding the above account, she said that she had not realized she had been so explicitly negative. We agreed that we had both been a little foolish! Who knows what might have happened had it not been for that silly miscommunication? Too late now — she’s still with the other guy she met shortly afterwards.)

During all this time, I had put Monelle as far as possible out of my mind. When it had first become apparent that I was not even going to be able to meet her, I had been devastated. In fact, I feared for my sanity. Somehow, the peculiar development and timing of the affair, with its drastic emotional ups and downs and frustrating anticlimax, had managed to hook me in a very unhealthy way. I kept coming back to thoughts of her (“If only . . .”, “Maybe the reason was . . .”, “Perhaps if I had . . .”), over and over and over, and each time it was like a stab in the heart. This obsessive mental loop had gone on so intensely for so long that I was worried I might be permanently scarred in some way. Throwing myself into meeting lots of different women was one way to try to forget her, or at least to weaken the obsession.

At first it only worked sporadically — my mind would be distracted for a while, but then as I lay in bed at night I would still return compulsively to her and what might have been, if only . . . But after a couple weeks I noticed to my immense relief that the anguish was recurring less often and had mostly been reduced to a mere wistful sadness. I would still have dropped everything to meet her if I had had the chance, but if that was not going to happen, it was now seeming that other nice relationships were also possible.

At that point, I felt strong enough to return to the issue. If possible I wanted to resolve it, one way or another, rather than leaving it up in the air. I decided to write a full account of the whole affair in the form of a message to her. Not really expecting to change her mind, but hoping at least to elicit some sort of response that might provide a bit more closure. Or if not that, to at least sort out for myself what had happened and why. I worked on this text over the next two weeks while continuing my online dating encounters.

October 3. Met Melanie (CL), an actor, director and playwright from Marin County. “My real claim to a very fleeting fame is that I’ve just produced an original musical for our small Shakespeare theater in Mill Valley. . . . In this show I really got back into singing. I had quite a folk music past and I’d love to find a folk group or a few ‘folks’ to sing with.” We met at a café in Oakland, then walked to a nearby block party that included several of her theater friends. She was pleased to learn about our huge monthly East Bay folk music potlucks, and I’ve since seen her at some of those, as well as at some of the plays she’s been involved with.

October 4. Lunch with Andrée, a writer whom I had met many years earlier through a mutual friend in the Rexroth scene. I was very fond of her and when I heard that she had split up with her boyfriend, the possibility of a relationship had crossed my mind. We ultimately concluded that we would not be a good match, but in the process of settling that issue and sharing our experiences of relationships and online dating, we’ve become better friends than ever.

October 5. To the Berkeley Marina to meet Emily (CL), an unemployed teacher. She was active in left-liberal causes (volunteered for ACORN, went to Colorado to campaign for Obama), into an eclectic range of humanistic-spiritual practices (Unitarian/Universalist church, Co-counseling movement, Sufi dancing) and godmother to an Eritrean family with six kids. A friendly, “girl next door” type, bright but unassuming, approaching people and things with a delightful freshness and enthusiasm. Despite many differences of interests, I immediately felt very comfortable with her, and thought: “This is someone I could see spending the rest of my life with.”

October 8. Phone talk with Sophie (OKC), a Sonoma County writer and Buddhist practitioner who had spent some years in France. She was definitely interesting and (judging from her photos) quite attractive, but the conversation also gave me the sense that we probably had somewhat incompatible temperaments. I was actually a bit relieved by that, because at this point I felt really good about Emily.

October 13. Met Chantal (OKC), a French masseuse, at her home/studio. An interesting chat, but we didn’t have much in common besides speaking to each other in French.

Later that day, Emily came over to my place. It was pouring rain, but then it let up and we took a hike in Tilden Park, savoring the clear air and marveling at the flooded creeks. She told me she was currently seeing one or two other guys she had met via online dating. I said that I, too, was meeting various other women at the moment, but that I felt really good with her and thought there was definitely a chance for a relationship to develop. I think she felt somewhat the same at that point.

October 15. In the morning met Carol (Chemistry.com), a Native American linguist. Then to a different café in the afternoon to meet Maureen (CL), about whom more later.

October 16. Emily came over for dinner, then we went to one of her regular things: an evening of Sufi dancing. I had wondered if this involved frenetic, “whirling dervish” movements, but it was actually fairly low-key and tranquil — a combination of chanting and gestures while slowly moving around in a small circle, with the two or three musicians stationary in the center.

October 18. Completed my long message for Monelle and sent it to her. In it I recounted the whole story of our interaction from my point of view, including things that she would not have been aware of (the sleepless nights, the Zen Center talk). I won’t quote that portion of the message since it’s substantially the same story that I have already narrated above. Then, ending on a more upbeat note, I described the online dating ventures and related experiences I’d been having since that time, and concluded:

. . . It all feels like a new adventure. I don’t know where any particular encounter will lead or what will happen from one day to the next. And I’m talking about all sorts of relationships, not just potentially amorous ones but also with friends and acquaintances and even strangers. Making a point to be open to new encounters, but also developing closer connections with people I already know (e.g. arranging one-on-one meetings with people I’ve previously only seen in a group context). In the process, there have been lots of fun and funny serendipitous interactions (e.g. coming across people at online dating sites whom I slightly knew from the Zen Center or the folk music scene but whom I’ve since gotten to know in a new way via this new connection). Conversations have become more lively and interactive — dialogues rather than monologues. And it’s contagious — many of the people I meet in this new spirit also become more enthused about relating with me (including confiding in me lots of things about their own relationship experiences). When one person opens up it inspires others to do the same, and suddenly one’s whole milieu is enlivened. Strangers become acquaintances, acquaintances become friends, friends become closer and more intimate.
       So my unrequited infatuation with you has unexpectedly led to a new opening up in my life. For that I am grateful — though I would have preferred to have arrived at it a little less traumatically!
       These last two months have been one of the most intense and interesting periods in my life. The first part was an excruciating tragedy, though with some comical aspects. The second part has so far been a mostly enjoyable comedy, though with a still unresolved tragic aspect lingering in the background — a sadness at the thought that you and I missed out on something truly special and wonderful; a feeling that things might have played out differently if we had gotten to know each other before whatever happened that prevented it.
       Anyway, I thought I’d tell you about these developments because . . . well, why not? Perhaps you’ll be interested in hearing about them. Or perhaps you simply wish I’d go away. It’s hard to tell what you might be thinking. After your last message some of my friends advised me to forget you because you seemed to have decided to cut yourself off from me. Others held out some slight hope, noting that you had originally manifested some pretty enthusiastic interest: “Wait a month, then send her something low-key. Keep it light, don’t scare her off, let her have her space, maybe over time her interest will revive . . .”
       But after thinking about it, I’ve decided to forget all that “strategizing,” all that trying to guess what might have put you off or how to entice you back into communication, and simply to send you this final message. If you remain indifferent after this, I can’t imagine what else I could have done.
       You may feel that this whole story is pretty bizarre, if not downright insane, because it’s based solely on a few email messages. We never met, so how could I tell what kind of chemistry there might be between us?
       I agree! That’s why I wanted so much to meet you, and why it’s been so frustrating to be stuck in this Internet mode, which makes it so difficult to convey subtle emotional nuances and where misunderstandings develop so easily.
       I would still very much like to meet you. On any conditions you wish. (For example, you could specify that it would be one time only, or merely on a potential friendship basis.) If nothing else, such a meeting would provide some closure for me, and perhaps for you too, following an interaction that ended in such an anticlimactic and unresolved way.
       I would think that curiosity alone would make you want to meet the man you had thrown for such a loop. But if you need an added incentive, I’ve still got that bar of Belgian chocolate!

She responded a few days later. Except for briefly complimenting me on my “creativity,” she said nothing about the story, then stated that she did not wish to receive any further communication from me.

Not a very satisfying conclusion to the affair, which remained as mysterious as ever. But at least it put to rest any lingering hope I may have had. From that point on I pretty much stopped thinking about her and focused my attention on encounters with others who were more interested.

October 19. Met Marisela (CL), a South American woman whose emails had seemed unusually interesting and delightfully exuberant:

Hello enemy of the state and Zen practitioner (interesting combination) I’m curious about to know you. My French is in crisis. Spanish, Portuguese, Italian, Russian, Slovene and Spanish are in much better conditions. Russian is also suffering the lack of use. The tragicomedies of life interest me. I could be defined as magnanimous and intellectually alive, very alive. I hope as it seems to me, you have a good sense of humor. Do you enjoy nature and arts? Those two things are fundamental parts of my days. . . . I arrived a little over a year to California from Chicago where I lived a number of years. I lived in Russia, England and Scotland, Slovenia, Uruguay, Italy, Denmark, Malta, Argentina, Brazil and visit some other countries with my work as Theater Director and teacher the J. Grotowsky techniques. I learned to speak the languages from where I lived. I went to elementary school bilingual French-Spanish for a while. I studied linguistic and occidental literatures, got certify as a Gestalt therapist. Today, here; I teach, translate and interpret English-Spanish. I’m writing a solo show. I’m preparing a psychodrama and performance workshops. . . .

I said to myself, “I’m not sure if she’s my type, but I should definitely meet this woman!” And I was right. At our first encounter we talked for over three hours. She turned out to be a wonderful person and has become one of my best friends.

October 23. A San Francisco woman wrote me (based solely on having seen my profile on Match.com): “Hello. I’ve always resonated to the writer-in-the-garret type of guy. Here I am again, at our age, feeling a connection with the likes of you. After all these years, is it meant to be for me? Or, are you an illusion? Dunno. But, I would sure like to put this fascination to bed before I die and/or live it with extreme passion and commitment. Any interest in helping me cross that bridge?” Judging from her profile, I was not interested, and at first I simply refrained from replying. But mulling it over a few days later, I thought it might be better not to leave her hanging. I wrote back to her, in part: “I want to warn you that it is quite unlikely that I would be interested in a relationship with you. I want to stress that fact because I myself recently went through a very traumatic period where I got hooked on a fantasy relationship with someone who responded enthusiastically to my personals ad and who seemed like the woman of my dreams. Ultimately I never even met her, and the letdown was devastating. For your own sake, please do not develop such a fantasy about me, because it’s not going to happen.” She replied: “Ken, thanks for your candor and fair warning about my fantasies. You may have saved my soul; if I have a soul. Good luck with sorting out all those other women.”

October 24. Met Tonya (Chemistry.com), a professor and public health researcher who had spent several years in India and Nepal studying Tibetan Buddhism.

October 25. Took Emily to a huge Halloween folk music party in San Francisco.

October 29. Met Emily at Berkeley Zen Center and showed her how to do zazen. Since this was apparently the first time she had sat still so long in silence (a forty-minute period), she promised herself that after she got through it she would allow herself to run down the street shouting. When she told me this afterwards, I took her hand and we both charged down the street screaming — except that she was mostly cracking up at seeing the zany manner I was doing it. Then we had a light dinner at Berkeley Bowl and went separate ways, she to a Co-counseling meeting, me to a fiddle tunes jam.

November 3. Met Mare (CL), a Zen practitioner and blog writer who likes boating and kayaking and used to live on a house boat.

November 4. Met Maureen again. After our first meeting, she had written me two or three follow-up messages, clearly disappointed that I hadn’t called her again. I replied that I had enjoyed our conversation but was not sure if our personalities or lifestyles were quite on the same wavelength; but that I’d be happy to see her again if she felt differently. At this second meeting, in the evening at the Bateau Ivre, I had mixed feelings. I was somewhat comfortable with her, but not fully; somewhat attracted to her, but not strongly. But I thought I might be game for a fling if she was so inclined. We parted and made another evening date for a few days later. The next day I mentioned the upcoming date to a friend and she asked if I was sure that Maureen understood the situation as I did. I said that I thought so. But just to make sure, I called her that evening and said that I hoped she understood that I did not see this as a potential long-term relation. She said she was well aware of that. But my bringing the matter up like this apparently rubbed her the wrong way. The next day she sent me an angry email canceling our date and adding several insulting remarks about me, my ad, my writings, etc.

That was virtually the only online dating encounter I’ve had that has engendered bad feelings. (I’m happy to say that we eventually exchanged mutual apologies.) The first lesson that I drew was to pay more attention to my gut feelings. I had not really been very enthusiastic about seeing Maureen again, but had let myself go along with it almost on the principle of the thing, thinking that if she was really interested, why not go for it and see what happened? I’m still trying to maintain that kind of openness, but at the same time to be more clear when I do not feel completely comfortable or enthusiastic.

My interaction with Maureen was no doubt pretty lame. But part of the problem here is that, in contrast to my younger days when I often had a fling with someone without there being any assumptions, most of the women I meet nowadays do have assumptions: they are looking for a steady, long-term relationship. As am I. Obviously, you find out if such a relationship is possible by starting with a short-term one and seeing how it works. But it may be unclear how explicit you need to be about expectations, or if or when to take an initiative in that direction if you sense that the other person may be particularly vulnerable if it doesn’t go well. On the other hand, excessive caution may result in missing out on a relationship that might actually have worked — sometimes people really relax and get to know each other only after they’ve become lovers and gotten beyond the preliminary courtship role-playing. So it may be a delicate judgment call, and I still don’t pretend to be very competent about figuring out what to do and when.

November 7. To Marin County to meet Cindy (Match.com), a teacher with Buddhist sympathies. We chatted while hiking in one of the many lovely woods areas over there. Somewhat untypically for a Bay Area woman in this politically correct and postfeminist era, she believes that there are very significant personality differences between men and women, as expressed in Alison Armstrong’s workshops and videos (a perspective somewhat similar to the popular book Men Are From Mars, Women Are From Venus). That sort of thing can ring a bell — you realize that there are indeed sometimes miscommunications because the two sexes are on different wavelengths — but I think that such differences are exaggerated and that there are a lot more similarities than these pop-psychology formulas allow for.

I don’t mean to disparage popular self-help books. Though they are often ridiculed, I believe that many of them contain good advice. As the original master of the genre, Dale Carnegie, said long ago, it’s strange that so many of us pay so little attention to how we relate to each other, considering that how we do so has so many crucial impacts on our lives. If you’re interested, one of the books on this topic that I’ve found most useful is Brief Encounters: How to Make the Most of Relationships That May Not Last Forever (Emily Coleman & Betty Edwards, 1979). It examines the whole range of relationships, not only amorous ones, with tips on everything from adventurous methods for meeting strangers to reevaluating priorities among your existing networks of friends.

November 8. Met Emily at a folk music gathering, then to Tilden, where we cuddled by Jewel Lake as the sun went down. That was our last time together, though neither of us knew it at the time. We planned to get together again soon, but it kept getting postponed due to other commitments she had and then the December holidays. By the time January came around and there were a couple of other postponed encounters, I realized the relationship was over. When I occasionally called or emailed her in the following months, she reiterated the impression she had given me that she was pretty content with her full schedule of connections and activities and preferred not to add other commitments. She had also discontinued online dating, so I don’t think it was just me. She said that she had enjoyed the times we spent together and that there was no particular incident that had put her off, but she had apparently not been as enthusiastic about seeing me as I had thought at the time.

November 11. Met Michelle (Match.com). She had composed a very charming profile and a few days earlier I had gotten into an email exchange with her. At first she had been friendly and receptive, but after a few messages she checked out my website (in this case, I had not sent her the website link, but she had found it via Google) and concluded that we would not be a good match. “You make me feel like a shallow dilettante. I want to go to nice restaurants and the opera and you want to play the overthrow of the government.” I convinced her that the differences between us were not necessarily fundamental, and we met at a nearby café (it turned out that we lived in the same neighborhood). The encounter went pretty well and we agreed that we would see each other again and see how it went.

November 17. Dinner with Michelle at Genki. She continued to feel that we were so different as to be incompatible, but said she was nevertheless enjoying being with me.

November 28. Met Diana (Chemistry.com). A few days earlier I had come upon her profile, one of the few I’d seen at any of the online dating sites to specifically evoke radical politics, and in the ensuing correspondence we came to realize that we had even had a brief email exchange a couple years earlier in a radical connection. When we met, we had what I thought was a good initial conversation. She was friendly, attractive, well-read, very intelligent, and the chemistry was definitely there for me. This all seemed very promising. We had conflicting schedules during December, but agreed to get back together after the holidays.

Unfortunately, when we got back in touch in January she wrote me that “on reflection” she had concluded that we would not be a good match. This was a real disappointment. Of all the women I had met up till then, she had seemed the most likely to be a congenial partner. That was of course only an initial impression — I had only met her that one time — but I had the sense that we might be kindred spirits and I could envision a really collaborative relationship. Whereas if I imagined a partnership with Emily, for example, it would certainly have been very lively and upbeat, with lots of fun and lots of laughs, but would probably have required much more juggling among our rather different interests and priorities and networks of friends.

As you have seen, in both of these cases my fantasies turned out to be delusions (at least partly). I’m mentioning them here as examples of how this exploration has been a learning experience for me — learning from failures and fiascos, but in the process also refining my sense of what I’m looking for, what sort of woman might be right for me, as well as what sorts of problems to watch out for.

November 29. A long hike by the Bay with Michelle.

December 1. To San Rafael to meet Deirdre (eHarmony), a writer and psychotherapist. We hit it off pretty well and saw each other three more times over the next few months. As in many of my other encounters, when the topic of online dating came up and we were sharing a few of our experiences, I briefly recounted the Monelle story. Responses to that story have varied. Most of the women I’ve met seem to find it intriguing, but in some cases they may also be put off by it, questioning my obsessiveness or perhaps wondering if they could compete with such a fantasized ideal. Deirdre, on the contrary, said it convinced her that I was serious about seeking a relationship. A few weeks later she even suggested the idea of dramatizing the story:

I have been thinking about the story you told me about the woman who wrote you online — the one who seemed so totally perfect — and all you went through regarding that. I think this story could be the basis for one of the vignettes in the theatre piece about couple relationships I am working on. It would be unique in that it would probably be the only piece about someone who was not already in a relationship. Would you be willing to tell me that story again and let me videotape you as you do? I know you have a written version, which I’d like to have as well, but I am also interested in how you tell the story — facial expressions, tone of voice, timing, all of that, because this would be of help to an actor, who would essentially be trying to re-create you and your experience.

I declined to take part in such a project, intriguing though it might have been, but her enthusiasm helped convince me that the story might be interesting to more people than my immediate friends.

December 6-12. Took part in the annual seven-day sesshin at Berkeley Zen Center. On the final day there is a ceremonial dialogue in which each participant comes forward to ask the teacher a question. When it was my turn, I made the following statement (the teacher was quite aware that I was metaphorically referring to Monelle and my recent online dating experiences):

During the last year or two I’ve been out in a boat fishing in the ocean. At first, not a whole lot happened, but then, about three months ago, I hooked a whopper! I never saw it, but judging from how strongly it pulled my boat, I could infer that it was a real beauty. I hung on for nearly a month — and then it got away. Since then, I’ve continued fishing more than ever. I have three questions for you:

1) What kind of hook should I use?

2) What kind of bait should I use?

3) When I catch some, how should I decide which one to keep and which ones to let go?

He answered: “For a hook, use a straight pin. For bait, use salt. And keep the one you have no doubts about.”

The straight hook is an old Taoist parable, usually interpreted to mean that there is nothing sneaky or underhanded, that a fish will be caught only if it wants to be. Salt as bait I take to be equivalent to no bait (salt being like what’s already in the sea) — basically the same meaning as the straight hook. In his third answer, I don’t believe that he meant only if everything seems perfect, but rather that the possible relationship seems on the whole so solid, so rich, so wholesome, so healthy that I will have no doubts that it’s worth working with, despite whatever problems there might be. (He later confirmed all these interpretations.)

December 15. Dinner with Michelle. She asked me about the sesshin and I described it, concluding with the above-quoted dialogue. This led to further discussion of what we each were looking for in a relationship. Our connection had remained warm and cordial despite our differences of tastes and temperaments, but I think by this point we were arriving at a stage where it was going to go one way or the other: to cease worrying about the differences and come closer, or to drift apart. It ended up being the latter. My guess is that I could have taken the initiative to come closer. I did not do so, and I think she may have been discouraged from taking such an initiative herself by her awareness that I had some doubts about a relationship with her and was still actively meeting other women, as implied in the sesshin dialogue. When I look back, I don’t think we would have been suitable partners for each other, but I am still touched by the pathos and intensity of our few encounters.

December 27. To Oakland to meet Paula (Match.com), a mental health worker who hosts a weekly meditation group with some of her neighbors.

December 28. Met Kay (OKC) at an erotic poetry open reading (her idea). There were around thirty people there, and about half of them read something. Kay read a piece she had written about some of her past relationship experiences. I read one of Rexroth’s more erotic love poems and a couple of his translations from Petronius, and sang a bawdy folk song. After the reading was over, she and I went to a nearby café to talk.

January 17, 2010. To Novato to meet Rosa (Chemistry.com), a recently widowed European woman who has lived in America most of her life. She was nervous — I was the first person she’d met through online dating. As in other similar cases, I tried to reassure her and gave her some advice and encouragement, including recommending that she shift to OKC. Then I proceeded on to Petaluma for a Scottish musical festival (Robert Burns’s Birthday), which was why I had been up in that area in the first place.

January 30. To San Francisco to meet Nicole (Match.com), a writer and long-time Zen practitioner. It was a pleasant encounter, but afterwards, considering our political and lifestyle differences, she questioned whether we had much in common besides Zen practice: “I guess I am thinking about whether you read the Times or watch Meet the Press, etc. When you saw the book I bought you immediately dismissed it as unworthy. What will we talk about? Can’t really discuss Zen all the time.” I replied: “I don’t watch Meet the Press etc. because I don’t have a TV. I sometimes read NY Times articles online. I didn’t mean to imply that the book you bought was ‘unworthy,’ but simply that that sort of thing — the sorts of things that Bill Moyers recommends — though often pertinent and informative, do not usually go to the root of the problems they discuss. They generally envision a solution in the form of some new laws or regulations that could be implemented if only we could get a Democratic majority in power. We have recently seen how well that works. What we might talk about remains to be seen. But there are lots of things in life to do and discuss in addition to politics. Some of my best friends are liberals and we find plenty to talk about! It may be that we wouldn’t have that kind of chemistry, but I’d like to get to know you better before jumping to conclusions.” A week later I met her again at a Zen Center celebration in Greens restaurant. I was somewhat interested in her and somewhat attracted, but also somewhat uncertain, seeing areas where we might not have jelled very well. I think she felt the same way. It was really borderline: If either of us had taken further initiative, I think the other would have responded. But neither of us did, and that was the last time we saw each other.

February 6. Met Lauren (Match.com), a semi-retired social worker and classical music lover. She has since been among the most enthusiastic readers of the Rexroth columns I’ve been posting every week over the past year: San Francisco Fifty Years Ago.

February 7. Met Joanna (eHarmony), a writer and editor. We hit it off pretty well and agreed to see each other again.

February 8. To San Francisco to meet Dorothy (CL), a teacher and author known for her innovative educational theories.

February 13. Met Melissa (CL), a nurse who lives in the San Jose area.

February 18. Met Vanna, an art teacher and Zen practitioner — not through online dating, but in a more old-fashioned way. One of my Zen friends, Beatrice, was playing matchmaker and had put us in touch with each other. Considering that Vanna is a very attractive woman in her 30s, I was both surprised and flattered that Beatrice had thought I might be an appropriate match for her. She claimed she had thought I was in my 40s! I had in fact just turned 65, and most of the women I’ve met via online dating have been in their 50s or early 60s. Relationships with greater age disparities are certainly possible, but I doubt if they are likely to work unless there is a pretty strong interest and initiative on the part of the younger person. (That was the case a few years ago when I had an affair with a woman who was 34 years younger than I. It didn’t last very long, but the age difference had nothing to do with the breakup. She is still a good friend and is now happily partnered with a friend of mine who is slightly older than I am.)

(Note to young readers who may be as clueless as I used to be: I remember that when I was much younger, people over 40 seemed pretty old and I assumed that people over 50 or 60 were no longer interested in sex; or that if they were interested, they were no longer capable of it; or that if they were capable, they were no longer likely to be able to attract anyone as a lover. That was just my ignorance. It is true that the sexual drive diminishes with age and people become less agile and more wrinkled, etc. But these changes are usually very gradual, and all the same emotional and relational complexities remain, even if things slow down a bit.)

February 19. With Joanna to a campus lecture on classical music, then dinner. Among many other things we talked about, I pointed out some of the limits of a social issue she is very involved in. She later wrote me: “I brought up the term ‘Situationist’ in a discussion with my sister’s family. We looked up a definition and I found myself understanding more of what you were telling me at that restaurant. In thinking over that discussion, I have been intrigued with the way you pushed me off a fence post that I did not realize I had perched on.” An admirably open and undefensive reaction.

February 22. Met Ellen (Match.com), an educational counselor who had lived in England, Provence and the Middle East.

February 26. With Joanna and a couple of her friends to a Zydeco dance in Alameda.

March 20. Dinner at Joanna’s home. This was another borderline case. We had some affinities and got along reasonably well, but there were also enough differences of interests and personalities that we were not feeling completely comfortable with the relationship. And did not continue it.

April 15. To San Francisco to meet Jamuna (CL), a freelance tutor and editor who had lived in Morocco and studied Indian vocal music.

April 16. To San Francisco to meet Miranda (Match.com), a music teacher who had spent some time in France. She seemed quite congenial and I expressed interest in seeing her again. She said she’d sleep on it. A couple days later she emailed me that she had concluded that we would not be a good match. My guess is that her decision was mostly due to my political remarks. She had asked me to tell her about the situationists, but my explanation may have gone on too long and reinforced her impression that we were in rather different worlds.

That’s just a guess — her decision may have been based on other factors — but this issue is in any case an ongoing dilemma. The situationists have had such a crucial influence on my life that it’s almost impossible to avoid mentioning them when someone asks me what I’m passionate about, what I spend my time doing, what sorts of things I write or translate, what my views are about various social and political issues, etc. But trying to explain the situationist perspective in a few sentences is like trying to explain Zen! I’m happy to make the effort if someone is really interested, but I don’t always succeed very well. A brief summary is almost inevitably misleading, while a longer one may seem overwhelming. One of the reasons that I continue to refer people to my autobiography is that it gives at least a preliminary idea of this perspective and how it has interconnected with my life, so that I don’t have to take up a whole conversation explaining everything from scratch.

Not surprisingly, many of my past relationships have been with women I’ve met in the course of my situationist-type activities. But although there was a lively international “situ milieu” in the 1970s, there hasn’t been much of one since then. Situationist themes have spread around the world and influenced subsequent radical currents, but those newer currents have mostly been much younger and culturally rather different. I can relate to them in some ways, but in other respects I’m out of my element. I have never had the slightest interest in Punk or Rap, for example, or the lifestyles and attitudes associated with them, just as most of those younger rebels are oblivious to a lot of the things that interest me. So while it would be nice to find a partner who was also a knowledgeable radical collaborator, it seems less likely to happen nowadays.

But at a minimum, it’s hard for me to imagine a partner who does not at least have some sympathetic understanding of the kinds of projects to which I have devoted much of my life. I don’t necessarily mean complete agreement. Someone who recognizes the systemic nature of the numerous problems in the world may be compatible even if we disagree about particular tactics. But someone who takes the present system for granted, and who imagines that fundamental problems can be solved by electing different politicians or changing a few laws, is probably going to be incompatible.

April 25. Met Jessica (Match.com), a yoga teacher who had been an active participant in the Berkeley Free Speech Movement back in 1964.

April 27. Met Corey (Match.com), a gourmet baker, who turned out to be an old friend of one of my Zen friends.

May 9. Met Jan (Match.com), a bluegrass fiddler from Sonoma County, who had come to one of the huge monthly East Bay folk music potlucks that I had let her know about. She has since been a fairly regular participant in those gatherings.

May 16. To a “cuddle party” at my friend Lee’s in Oakland. Despite what one might imagine, there is no sex. There is a workshop component to it in which participants learn to explicitly communicate what they want or do not want, but mostly it’s simply a fun way to relax and get a lot of hugs and massages and playful group interaction without the pressure that may come from sexual expectations or implications. One of the other participants was Marisela (I had introduced her to Lee at the Anarchist Bookfair a couple months earlier and they had become good friends).

May 19. To San Rafael to meet Tia (Chemistry.com), a freelance photographer with Buddhist sympathies.

June 9. One of my daily “suggested matches” on one of the dating sites turned out to be — Monelle. She had just signed up. I had long ago gotten over my obsession with her and had come to suspect that a relationship with her might have been problematic in any case, but I was still very curious and examined her profile with great interest. It provided a fuller self-description than the brief emails I had received from her almost a year earlier, confirming my original conviction that she was a very remarkable woman but also giving me the impression that we may have had more significantly different temperaments than I had imagined. For a while I didn’t do anything, since she had indicated that she wanted no further communication. But after a couple months I decided what the hell, and sent her a brief, upbeat message, wishing her luck and reiterating the fact that my interaction with her, though traumatic, had had the happy effect of propelling me into a more lively and active exploration of relationships. She sent a brief but friendly reply: “Thanks for checking in. Glad to hear that things are going well. Take care.”

It still strikes me as strange that one of the most influential people in my life lives right here in the Bay Area and I’ve never had a chance to meet her! On the other hand, if I had met her, the rest of this adventure might never have happened — the intensity with which I plunged into online dating was probably due to her very elusiveness. So while I remain curious, I also remain grateful.

June 10. Met Silvia (OKC), an architect and writer.

June 16. Met Julia (CL), a writer who among other careers had spent several years in the Air Force.

June 17. Met Monica (CL), an artist, at her home in El Cerrito. Oddly enough, one of my folk music friends lives right next door to her — while we were having tea in her back yard he leaned over the fence to say hi. Another coincidence: back in the sixties she had wanted to go to Shimer College (my alma mater) but her parents did not approve. If they had let her go, we would have been classmates there over forty years ago.

June 18. Met Lila (CL), an artist and computer animator. Some time later she told me that she thought she knew who “Monelle” was. She was mistaken, but there were indeed a number of similarities in the two stories: Via online dating her friend Cynthia had met a man who sounded somewhat like me (well-read radical author living in Berkeley), there was a suspenseful delay in communication while Cynthia was at a Buddhist retreat, etc. Cynthia was not Monelle, but she turned out to be an acquaintance of mine in the Zen scene.

June 29. Met Ana (OKC), an ESL teacher, classical singer and Buddhist practitioner who spends her winters on the beach in Mexico.

June 30. Met Janie (CL) at the Berkeley Pier, then continued the conversation over dinner at Picante. Her original response to my ad was: “Reader for blind woman, writer of technical manuals, Engineer-speak translator, beginning fiddler, backpacker, quilter, Zen-ignorant fan of guided meditation, and mild-mannered enemy of intolerance seeks a meeting with you.” Later, when I was getting her okay for this description, she replied: “You might also mention that you gave me your book [Public Secrets] and put me on your mailing list for musical events, for which I am grateful.”

July 7. Had my friend Danny over for dinner. He was the guy who, nearly a year before, had suggested that I try OKC. At that earlier time he himself had had only minimal experience with online dating. Now, however, he had broken up with his girlfriend and had just signed up on OKC, so I was able to return the favor by giving him some pointers.

July 8. Met Keln (CL), a well-read Russian math teacher.

July 9. Met Roxanne (OKC), a professional musician who had spent some years in France. She has her own trio and likes to sing French and Spanish songs, but her regular job is performing popular numbers from the 1930s and 1940s for older adult communities in the Napa Valley.

July 14. Marisela had recently begun offering me and a few other friends weekly “Danzas de la vida” workouts — a physically and emotionally exhilarating combination of aerobic dance-exercises and solo and group improvisations. On this occasion Lee was also there and one of the other participants, a charming young radical artist named Edna, turned out to be a friend of Alex, a French friend of mine living in San Francisco whom I had originally met through the Zen scene, and whose mother Fanny used to frequent the same Paris bar as Guy Debord and the other lettrists back in 1953. . . . These sorts of tangents go on and on in all directions. I mention them here simply as an example of how one connection leads others. In this case, my original meeting with Marisela ultimately expanded the social networks of Marisela, Lee, Edna and myself, leading to yet other encounters. . . .

July 15. Met Celia (CL), an artist, gardener and Buddhist practitioner. A few weeks later I attended a showing of her paintings (exquisite acrylics of sea creatures).

July 18. Met Priscilla (OKC). I had originally contacted her on OKC back in November, but then her profile had disappeared and I had assumed that she had found someone else. It turned out that she had simply had some family issues to deal with. In early July her profile reappeared and I recontacted her. She is a teacher with a PhD in linguistics, a Buddhist practitioner (Tibetan style), attractive, well-read and fluent in French. Not politically active recently, but used to work for the Greens. Very much the bright but quiet, low-key type I like. The encounter went well, she was interested in getting together again, and I felt pretty optimistic. Though I had just gotten to know her, I could already envision her as a possible partner.

July 19. Met Christina (eHarmony), a Buddhist practitioner and NGO grant writer and fundraiser.

July 24. Met Priscilla for lunch at Long Life, then a hike in Tilden. She talked about her work options (she was in the process of phasing out one of her two jobs, hoping to make time to complete a book she had started on language and dreams) and her two college-age children (her daughter was going to Europe for a semester and she was considering the possibility of visiting her while she was there). We also shared reminiscences of the sixties counterculture (she was only a child during the sixties, but had been involved in the Grateful Dead scene which had carried on some of the same spirit into the following decades).

August 7. To El Sobrante to meet Zwicka (CL), a Slovenian woman who had been raised in Belgium. Living in Sonoma County, she misses the European lifestyle and cultural amenities and appreciated being able to talk with me in French.

August 12. To San Francisco to meet Parvati (Chemistry.com), who turned out to be the daughter of a fine teacher I’d had when I first came to California in 1965 (at the now-defunct American Academy of Asian Studies in San Francisco). She works as a computer consultant, but on the side conducts New Age-type workshops.

August 17. Met Priscilla for dinner, then to a Kipling play. (The director turned out to be Melanie, whom I’d met via CL nearly a year before.) Priscilla said that she had just run into a guy from her past and that she might be hooking up with him again. I said okay, that I would enjoy continuing to see her but would make no assumptions.

August 20. Met Priscilla again at same theater to see Noel Coward’s Blithe Spirit. A pleasant evening, but that was virtually the last time I’ve seen her, since she did end up renewing her relationship with the other guy she had mentioned.

August 27. Met Rachel (Match.com), a professional classical musician.

September 6. Met Deborah (Match.com), a San Francisco librarian.

September 11. To San Rafael to meet Lucy (CL), a music teacher.

September 12. To a church organ concert to meet Clara (CL), a classical musician.

September 13. Met Yoshimi (CL), a Japanese artist.

September 14. Met Jennifer (CL), a grade school teacher, mental health worker and lover of poetry.

September 15. Met Carolyn (CL), a writer who has worked for several international NGOs.

Incidentally, notice those last five encounters. Somewhat surprisingly, although CL is a pretty drab, bare-bones site, I’ve actually continued to meet more women through it than any of the dating sites, simply by continually renewing my same little ad. This is probably due to the much vaster potential readership — the fact that anyone in the world can browse CL ads and respond to them without being “members.” On the other hand, CL is not even remotely as rich and interesting as OKC and Match.com, which enable me to explore thousands of possible matches. If I haven’t met quite as many women through the latter sites, this is because examining the informative profiles has enabled me to quickly filter out in advance many women whom I might otherwise have met if we had depended on the slower and more minimal information conveyed via CL, thereby saving both them and me a lot of time. So what I’d recommend, if you’re interested in trying online dating, is to join OKC while continuing to run a brief ad on CL. (Match.com is probably the next best. I don’t recommend any of the other sites unless you, like me, are really going whole hog.)

September 18. Met Penny (CL), a San Francisco lawyer, at Hinkel Park in Berkeley, where we watched the Iliad-based play In the Wound. Then to a café. Despite the sophisticated nature of the play she had invited me to, she was worried that I would see her as too conventional, too much into pop culture rather than classics, etc. There were indeed some differences in that vein, but she seemed congenial enough that I was game to see her again anyway. A couple weeks later we got together for dinner and a comedy show (three female standup comedians). I don’t normally go for that sort of thing, but she had invited me and it was interesting to do for a change.

September 19. To Yoshimi’s home, where she served me a delicious Japanese lunch, then showed me how she does her sumi ink-painting, focusing on each brush stroke with grace and mindfulness. Ironically, although that painting style reflects a strong Zen influence, she had never done formal Zen practice. I invited her to come to Berkeley Zen Center to get a little taste. She did so and liked it very much. She and I have such significant differences in cultures, lifestyles and personalities that it would be difficult to picture us as a pair, but getting to know her has been very interesting indeed.

September 22. Met Brenda (CL), the owner of a teleprompter company, who had some amusing stories of her experiences working with prominent businessmen and politicians.

October 13. Met Conchia (OKC), an Oakland nurse. Her reaction to my autobiography: “Whew, hope there won’t be a test! Yes it is a bit much to encounter and it may be giving false clues as to your character. So I grew up in the same generation, yes Berkeley in the 60s. My approach was a different one but there we were in the midst of it all, anything went down.”

October 14. Met Giovanna (Match.com), a radical professor.

October 20. Met Nora (CL) at a radical library in Oakland where I was doing a reading/discussion of In the Crossfire: Adventures of a Vietnamese Revolutionary. Nora and I share many experiences from the Beat-Hippy era (she had known Lew Welch and once even met Kerouac) and we had corresponded several months earlier, but we had not previously met since she lives in Santa Cruz.

November 11. Met Stella (OKC), kayak enthusiast, worker for an arts NGO and grand-niece of W.C. Fields. She was new to online dating, but very open and upbeat about it, agreeing wholeheartedly with my own attitude about its possibilities and how to approach it.

November 20. Met Marsha (CL), an amateur artist and semi-retired computer programmer from Santa Cruz. Her response to my autobiography: “I loved your story. Yes it was a little self-indulgent in parts but so what. It’s always a privilege to read about another person’s life experiences. It took me a while to read because it caused me to pause often to ‘pursue my own flight’.” She also noted that she once solved a problem with the IRS in a similar way to how I evaded the draft: “I stood up, grabbed some things off the desk in front of me and started throwing them around, all the while screaming ‘why are you doing this to me’ over and over. I was very dramatic. They tried to calm me down, brought me some tea, and one of them went into a back office and came out promptly with a signed paper saying the levy was officially dropped.”

November 29. Met Lisa (Match.com), a bicycling enthusiast who, appropriately enough, works as a consultant promoting alternative forms of transportation and shares my appreciation for Paul Goodman’s article Banning Cars from Manhattan.

December 13. To San Rafael to meet Maryam (Match.com), a British-born psychotherapist and Buddhist practitioner now living in Marin County.

December 15. Met Ann (eHarmony), a 1960s radical who had later become a community and educational policy analyst and is currently working on a novel. A couple weeks later she sent me this message (she had followed my suggestion to shift to OKC): “Well after all that work I did on OK Cupid, my ex-boyfriend called for a date and we’ve reconciled! On the upside, I did meet some interesting people (including an old college friend) and also learned a lot about myself and what I want in a relationship and with friends. One of the bright spots was meeting you so I hope we can meet occasionally for tea at Café Leila!”

Later the same day I met Loretta (CL), a teacher, musician and songwriter.

December 29. To San Rafael to meet Gisella (CL), a registered nurse and planning commissioner with spiritual interests. In the latter connection, she described her recent trip to India and also some amusing incidents at a couple of Spirit Rock singles parties she had attended.

January 5, 2011. With Penny to see the sequel to the play we’d seen together three months earlier.

January 8. Party for my 66th birthday — an all-afternoon open house followed by dinner at a nearby Japanese restaurant. Among the invitees were over a dozen of my online dating friends. Those who were able to make it included Lila, Marisela, Susan, Yoshimi and Deirdre (with her new boyfriend, also met via online dating).

* * *

New encounters continue, but I’m going to stop the account at this point and wind up with a few thoughts about this whole adventure.

People who haven’t tried online dating often disparage it, extolling the advantages of meeting people “naturally,” in spontaneous contexts where you can gradually get to know someone. But online dating does not preclude any of those other ways. You can still meet people because you work in the same place or go to the same school or share some activity, or even by a chance encounter on the street or in a café. All that can still happen (at the slow pace it usually does), but meanwhile you can also be meeting many other people. Moreover, unlike in ordinary situations, where most of the people you meet are already taken and it may be unclear whether the remaining ones are available or interested, in online dating you at least both know from the beginning that you’re both seeking a relationship. This enables you to proceed directly to specific areas of concern and interest, and often to learn more about each other in an hour than you would have in weeks or months under more casual circumstances.

You might think that it would be really weird to start a conversation like that with a stranger, but it’s actually a lot of fun once you relax and get used to the idea. That, at least, has been my experience. If I had approached these encounters like job interviews, I would have gotten burned out pretty fast! The reason I continue to enjoy the process is because I’m keeping it light and loose, appreciating the interaction with each new person without worrying too much about whether or not she might be my ideal match. In fact, this distinction has become increasingly blurred — I’ve become so habituated to enjoying lively encounters that I sometimes decide to meet a woman who seems particularly interesting even if I suspect that a romantic attraction is unlikely.

It’s been easier to do this because I no longer feel the all-or-nothing desperation that I did in earlier periods when I was only rarely meeting a possible lover. During this last year I’ve probably met more potential matches than I did “naturally” during the whole previous decade. It’s been a process of self-discovery to see how my priorities work themselves out amid this unaccustomed abundance. For the moment I’m simply going with the flow and seeing if a deeper rapport develops with any of the women I meet. If not, I’ll keep looking. While I’m still hoping to find a long-term partner, I’m content to let each relationship find its own level.

I hasten to add that in all of these encounters I am completely up front about the fact that I’m in a temporary exploratory phase and continuing to meet other potential matches — as are most of the women I’m meeting. If and when a relationship develops that seems really promising, I will put other encounters on hold and focus on that relationship until I see how it works out.

Whatever ultimately happens, this venture has already been a success. If I haven’t found a partner, I think I’ve come close to it in a few cases, so I’m not discouraged. Meanwhile, I’ve made a lot of new friends while enriching my connections with many of my old ones. And I hope that in the process I have become more attentive in relating to people in general and to women in particular. (I don’t want to give the impression that I used to be socially inept, but simply that there was, and remains, a lot of room for improvement!)

Gradually, almost without my noticing it, this project has become like an immense Zen koan — a puzzle I have focused on so intensely, or a practice I have immersed myself in so fully, that it seems to have subtly reoriented my whole life. But unlike a koan, it’s not an exclusively “internal” process. How I approach these encounters is up to me, but the outcome also depends on other persons, persons who are just as complex and unpredictable as myself.

So I have no idea how this will all turn out. Perhaps I will find the soul mate I’ve been seeking. That would be wonderful, though like all things in life it would undoubtedly present its own new problems. Or perhaps I won’t. That would be disappointing, but not the end of the world. After all, I’ve been without one for a long time and nevertheless gotten along pretty well. In fact, I suspect that part of the reason I haven’t had such a relationship for such a long time is that I’ve been involved in so many other engaging pursuits. I would have loved to have a special someone to share those experiences with, but I didn’t really need such a person to feel reasonably fulfilled. So I ended up being pretty picky. I didn’t just want a mistress, but someone who would also be a best friend and collaborator, as had been the case with my two most substantial and enduring relationships long ago, Aili in the 1960s and Tita in the 1970s. I’m still looking for that kind of companionship, but I have meanwhile perhaps become a little more flexible. I realize that any two people are going to have some differences to work out — that’s the nature of relationships and part of what makes them so interesting!

I’m also aware that there are a lot of intangibles that are difficult to articulate or predict. Some of my previous lovers have not matched all of my preferences, just as I have undoubtedly failed to match up to theirs, yet our interpersonal chemistry more than made up for it. This is why I specify only a “magnanimous and intellectually alive companion.” Those two qualities are essential; other issues may be negotiable.

I don’t see a love relationship as an escape from the world, but as fostering a more intimate and accurate connection with it. By focusing on each other, true lovers also get a finer focus on everyone and everything else:

For the undeveloped heart,
The news or even the sight
Of the destruction of thousands
Of other human beings
May assume only the form
Of a distant cry . . . .
However, as the dual,
The beloved, is known and
Loved more and more fully, all
The universe of persons
Grows steadily more and more real.
(Rexroth, The Dragon and the Unicorn)

As my old friends know, I tend to periodically get into some enthusiasm and pursue it to the extreme. The present venture has certainly been a prime example of this. I’ve discussed it so much with so many of my friends that some of them are probably sick of hearing about it! But most of them have seemed to find it interesting enough. A few of them even asked me if I was going to write about it.

At first I brushed the idea aside. Not only would it probably expose me to ridicule and embarrassment, it might interfere with the very quest I was writing about. Women I had met might be worried about their identity being exposed, or offended at how they were described (or not described, in comparison with others). Others might shy away, concluding that there must be something wrong with me if I haven’t had a partner in such a long time, or that I’m apparently so picky that they have no chance, or that the competition is too stiff since I seem to be meeting so many remarkable women.

But the more I thought about it, the more the advantages seemed to outweigh the drawbacks. For better or worse, this text is an expression of who I am. Women who might be put off by it would probably not have been compatible with me anyway, while on the other hand it may strike a chord with more kindred spirits. As for ridicule and embarrassment, there is always that risk when you do something out of the ordinary. That’s part of what makes it an adventure!

Another part of the adventure has been reconnecting with many of the women I’d met. When this text was just about finished I contacted each of them, letting them know what I had written about them and asking if they had any comments or objections or if they’d like me to change their names. Most of them reacted positively, or at least neutrally, even if they must have wondered what strange sort of project they had ended up being part of. A few were at first concerned that their privacy might be invaded, until they realized that I was happy to eliminate any information that might cause them any problems — my fault for not being clearer about that in my original message. Some did not mind if I used their real names, but most requested pseudonyms, so I decided it would be simpler and safer to change all the names. (Many of them chose their own pseudonyms.)

As I noted in my autobiography, “And as far as possible I try to make each new project a new venture, choosing a topic I haven’t explored or a method I haven’t tried before. This makes it more interesting for me at least, and hopefully for the reader as well.” The present text has certainly presented new challenges in both topic and method. It’s the first time that I’ve publicly discussed this type of personal issue; the first time that I’ve had to consider so many other people’s feelings; and the first time that I’ve published an account of a venture that is still very much in progress.

The latter fact has prevented this text from being very aesthetically coherent. Although the Monelle episode had a certain dramatic intensity (for me, at least), it ended up propelling me into a looser and more episodic series of encounters that has been much more pleasant and illuminating for me, but probably not so interesting to read about!

I should also note that although I am continuing my search, I have no intention of continuing this account. I’ve spent quite enough time writing about this topic and am ready to move on to other things!

I could have taken a more “sociological” approach to this topic, examining how the present social system isolates and fragments people in various ways (so that they tend to come together primarily around their passive consumption of the same commodities and spectacles) or how being forced to work in alienating jobs robs people of the time and energy to cultivate meaningful personal relationships. But I didn’t. I undertook this venture for my own personal purposes, not as any kind of “social research” or “radical analysis.”

Nevertheless, the process of recounting one’s own experiences often has surprisingly far-reaching effects. Not only is it clarifying and liberating for oneself, it can also give others the inspiration or “permission” to undertake their own experiments and self-examinations.

Countless people face these same issues. Even if you are among the happy few who have an enduring and fully satisfying relationship, you surely know others who don’t. I don’t think I’m very different from millions of other people, many of whom have gone for years without any relationship whatsoever. I doubt if most of them really like it that way, they’ve simply grown resigned to it because present social conditions tend to keep people isolated from each other. Online dating may or may not solve their problem, but at least it gives them a chance to meet a lot more potential partners.

In any case, whether or not you find a romantic partner (or are even looking for one), just taking the initiative to put yourself out there often has unforeseen results. This is why I have noted a number of serendipitous coincidences in this story. I don’t think that such coincidences have any hidden, mystical meaning. They’re simply the sort of thing that happens when you experiment with your own life. New ventures lead to new encounters and new encounters lead to new adventures.

Such adventures have little resemblance to the spectacular adventures that are constantly being presented for our passive consumption. Part of what is exciting about them is precisely that they break through the spectacular façade and bring us into contact with real life and real people. They may be modest in scope and they may not always work out as we would wish. But better a striving for real connection, however awkward or pathetic, than the pseudoconnections people are drawn into when they are deprived of the real thing.

* * *

This text is dedicated to each of the women I’ve met in this process. It’s been a pleasure to get to know you, however briefly it may have been in some cases. I wish you the best in your quests for love and fulfillment and hope that you will forgive me for any ineptitudes in my interactions with you.

February 2011


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