There was a time during the middle of 2007 when every junior staff member at the magazine where I worked was looking for love on the internet. The art director, an amiable Scandinavian in his mid-twenties, set up a white umbrella lamp in his tiny 
office and snapped some pictures of our coworker Rob that revealed a pair of bee-stung lips and dreamy eyelashes we had never quite noticed while sitting hunched in 
the glare of our computers. Rob had wanted the pictures for online-dating purposes, and he posted them, next to descriptive text that made him sound noble and introspective (maybe, all this time, he really was noble and introspective). Within a few weeks, he began dating a beautiful Cuban law student. I felt a sense of envy, but not of loss. I didn’t quite want to date Rob. Sitting four feet away from me, day in and day out, he was too close already to want to bring into that other kind of closeness. But the rest of New York, it seemed, was too far away. Surely there were other offices on our block where people our age also toiled with computers and ideas. Why couldn’t we meet them? 
We could invite them to our office for 
Friday-afternoon beers, and the next week, they could have us over to theirs. Like 
many sensible things, it seemed impossible to arrange.

One by one, we all trooped into the art director’s office to have our dating portraits done. I still have the pictures. In a blue cardigan and a gray collared shirt, I look corporate and a little bit pale. I was having an unhappy few months. I’d left a tumultuous relationship; I was new to the city. So I turned to online dating with a sense of gritty determination which, in hindsight, probably wasn’t the frame of mind most conducive to romance.

“Kaffrin,” Rob used to IM me during the middle of the day, before he met his Cuban girl. He spoke fluent lolcat on IM, and little else. I’d look up from the computer, and he’d fix me with a sly, goofy expression, and then return to his screen and his keyboard to finish the message. “I AM GOING 2 DAI ALONE!”

Rob was a Match.com man; so was the art director. Trying to cover all the bases, I did Match and Nerve both. Another editor used the Onion (which plumbed the same dating pool as Nerve, but looked different). It livened up the workday to swap our stories, sharing crushes we’d developed, identifying our dates or prospective dates by code names borrowed from their self-descriptions: “Honduras,” “Lenin,” “model man.” Rob and another coworker, Erica, found significant others, I gave up after a while, and the art director moved back to Sweden, but there’s no question that it helped to pass the time, and even gave us a little of that good feeling that comes with taking matters into your own hands.

My first online date was my first date, period. It was 1993 and I was 14 years old. Our family had a home computer with a 3600-baud modem that squealed in digital ecstasy when it connected to a remote location. I was not the most hard-core kind of nerd girl, but I had gotten mixed up with some boys at school who knew things about computers.

Late at night, when my parents were sleeping, I would sit in their study and dial into what we called bulletin board services. They were essentially big graffiti walls with private-messaging capabilities, and most of the ones I went to were hosted by people I knew, or knew of: boys at my school or at cooler private schools in DC. We all took pseudonyms, the better to stalk each other through the shadow world. It was a world with no adults, radically so — like a co-ed Lord of the Flies, where instead of pointed sticks, we hunted each other with words.

One of the users was a middle school student in an outer suburb who went by the name Luke Skywalker. He didn’t know me, but he started to flirt. One night I opened my private mail and found a message from Luke: inside was a long-stemmed rose, made entirely of ASCII characters, blinking green and red; in the dark of the study, I blushed. I already knew that Luke Skywalker wasn’t funny or brilliant, but he was okay, and I appreciated his directness. So when he asked if he could to take me to a movie, I said yes. Our mothers drove us to Pentagon City — the nice mall — for our afternoon of romance. I still remember how quickly my heart sank as Skywalker and his mom walked toward us on the mall’s tile floor.

Luke was chivalrous; I was polite, awkward, and secretly hostile. Our date came to a dramatic end when we stopped, during our post-movie stroll, to gaze over the food court. I eased my bare knee between two of the uprights in the metal railing we were leaning on. Then I tried, just as casually, to pull it back out. There was a tug, and then a pinch. A firmer tug, answered by a twinge of pain. I kept pulling and tried to look nonchalant. “Are you all right?” Luke asked, noticing my struggle. He knelt down and started prodding my knee, which was now red and swelling. Failing to effect a rescue, he left me to flag down the mall cop who eventually freed me, shaken and humiliated, from the railing. Luke and I parted ways near the Aéropostale, and I never spoke to him again.

My online dating spurs collected dust until 2005, when I moved to San Francisco and decided to give it another whirl. I chose Craigslist, the only personals site I know of that doesn’t adhere to a social-network formula. There are no profiles, and rarely any pictures. It’s old-fashioned: just you and your ephemeral, textual ad. I think I believed Craigslist would be a nice compromise between a dating site and an all-purpose source of community. Its reputation as a nasty, hard-core pickup scene had somehow escaped me.

I posted my ad in the women-seeking-men section. It said — I wish I were kidding about this, but alas I’m not — that I was “new in town,” and looking for someone to show me around and tell me where the good stuff was. I added a line that I saw on a number of other ads: “Your photo gets mine.”

I received pictures of body parts. Most of them were dicks, though some were indeterminate, and there were a few chests and biceps in the mix, too. Some of them were pictures of entire people. One was suspiciously attractive, a little too glossy to be true. I got responses from recent immigrants still learning English. I decided that I needed to amend my ad somehow, by adding a cultural touchstone that would broadly but accurately define what I stood for, and what I sought. The following week, I ran the same ad, with one addition: It would be good, I said, if you were the kind of person who, say, enjoyed the music of the Velvet Underground.

A few days passed, a few more dicks in my inbox. I was considering withdrawing my ad when an email arrived, forwarded from Craigslist’s anonymity-preserving email bot. The message was properly spelled, and composed in several balanced paragraphs. It opened with an amusing anecdote, segued neatly into a self-introduction, and concluded with an appeal for my reply. Its author had appended a photograph: a black-and-white shot of a serious-looking, thoroughly handsome young man in hipster glasses, with a cute, rounded nose and a head of tight curls.

Naturally, I wrote back.

At our first date, at a tiki-themed bar north of Berkeley, which I pedaled to on the road bike I’d appropriated from my roommate’s shed, Eric explained how he’d come across my ad. He’d gotten home from work one day, and had time to kill before heading out with a friend to see a concert. He sat down in front of his computer and meandered onto Craigslist. Idly eyeing the iconic banana poster on his wall, he typed “Velvet Underground” into the search box. Two posts appeared: mine, and another personals ad from a 40-year-old drug addict. He only wrote to one of us.

Eric and I had a couple of pints in the bar. He was working as an urban planner. I was working as a magazine intern. We were 25 years old. We discussed Jane Jacobs. Drinks were a success, so we walked down the street and got a meal at an almost-deserted Thai restaurant. Eric was a great improvement on Luke Skywalker and his mom. I left the date thinking, yes. Yes. I would do that again. On the way home, I ran over some glass and flattened the tire of my bike. I walked a long way down creepy, unfamiliar San Pablo Boulevard. Eric and I dated for almost two years, until I decided to move back to New York City and long distance pulled us apart.

Even in San Francisco our romance was not without its critics. My roommate, for example, was a great opponent of going online to meet people. He believed that computer-aided romance was destroying the fiber of our collective being. He saw it as a crime against love, which he thought ought to be singular and spontaneous. To him, Match.com had all the romance of comparison-shopping paper towels in the aisles of Wal-Mart. “Assuming you did meet someone,” he’d say, banging the lid onto a pot in the kitchen, sincerely upset. “What would you tell your grandchildren? How would you say you met?!” I tried not to make a quip about how I would at least have grandchildren. While I was out with Eric, my roommate could usually be found drinking whiskey and watching Six Feet Under in a straight-backed chair on our enclosed porch.

A couple months ago, I dusted off my profile and eased back into online dating. I added a new picture—I’m told I’ve got the color back in my cheeks — and am trying to remain easygoing about it. I’m enjoying the sense of possibility, and the familiar weirdness of the ritual. I do a little OkCupid, a little Nerve.com. Some weeks real life distracts me and I don’t do anything at all. Fifteen years after that first date, I take this way of meeting people for granted, as just another part of how we live.

But the rituals and conventions still fascinate me. There are things one says: everybody mentions that they’re equally at home in a dive bar and a fancy restaurant, that they love the city but also cherish their time away, that they’re creative despite working in an office, or levelheaded despite being free-spirited. These are clichés, but they’re necessary, if only to make this weird, unnatural pursuit seem normal and ho-hum. If you want to flout them in an attempt to be witty, you’d better hit it out of the park. Because in some ways, the dating site is as courtly and mannered as a Victorian drawing room where women communicate with the angle of their fans. The way to express yourself is to deviate, just slightly, from the norm.

And yet I honestly puzzle over what the formulaic statements actually mean. What is it to be laid-back, and why do two-thirds of people on personals sites identify themselves this way? If “I’m laid-back” is code for “I’m not stuck up,” or “I’m sort of embarrassed about being on this dating site, so let’s all just pretend that we’re here for a lark,” that seems fine. But it’s cryptic. And “I don’t take myself seriously” even more so. Isn’t taking oneself seriously—in this, the only life we have been or will be given—a good thing? There are, of course, people who overdo it the other way. I’m as leery of someone who lists fifty favorite bands, alphabetized, as I am of someone who posts only two sentences of self-description. There’s a language inside the language, if you know how to hear it. And you learn. Everybody’s laid-back. Nobody’s coming on too strong. So you listen hard for the messages between the lines, coded in the fans’ tidy fluttering.

A couple of weeks ago, just for fun, I looked at Craigslist again. I wasn’t searching for anything, just getting out of the drawing room to take some air.

I can’t believe that I once used Craigslist for dating, much less that it actually worked. Because it’s basically image-free, and totally, radically anonymous (as opposed to the gentle twilight of regular dating sites, where I’m always stumbling across people I know in real life), people on Craigslist get, shall we say, right to the point.

My recent visit turned up quite a few tantalizing offers. A sampling:

Brooklyn wants to watch you masturbate. (This is all just “men seeking women,” by the way. I didn’t even look at “casual encounters” or “misc romance.”) The Bronx will travel to your location on lunch break to dine on you. Williamsburg is at home with a chest cold and would like to chat. Gramercy Park wants to meet for a drink tonight, and, if all goes well, get cozy in his bed. Too tame? The Upper East Side wants you to “come over, lay down, get completely orally devoured, and then walk out the door: no questions, no strings, no drama.” Pretty much every part of the city is bored and wants it now, tonight, today. Scarsdale demands complete submission. Downtown seeks an adult breastfeeding relationship. Nassau wants to “give pleasure to a fat, sloppy, and ugly woman where she will experience pure and total ecstasy within.” Jersey City would like to be your houseboy, and will do whatever you want, but has a list of helpful suggestions: dishes; massaging you; windows/floors; drawing your bath; oral pleasure; laundry.

I sort of love it, this sense of a secret universe inside the city. And I love the specificity of the desires: it’s tonic after the laid-back, cloudy, “looking for someone to complete me” feeling of my regular places. It seems so wonderfully simple to be looking for a specific act, rather than a perfect actor. Finding a hyperthyroidal transvestite who likes to give foot massages is more straightforward, and arguably easier, than finding Mister Right.

But as I keep on reading, I realize it’s not just sex. Craigslist’s anonymity frees people to express every manner of desire, from lewd to existential to just plain romantic. So there’s a second family of ad here, to complement the “Where can I meet you in fifteen minutes?” type. It says: “I’m lonely. I’m ready. What are you doing for the next fifty years?” Forty-one in New York City writes: “I feel I am missing out on precious time being alone. I can’t wait to deeply love and respect a good woman again.”

Twenty-six, downtown: “I am actually looking for a LONG TERM RELATIONSHIP and possibly marriage too. I want to fall in love again and not in lust. It is not hard for me to get women to sleep with . . . I just don’t want that in my life. I want love and only love.”

A single black man in Harlem seeks “a Black woman who will love me like I will love and adore her. The love that I’m looking for is a cornerstone of the life that I would like to build with her. This love will sustain the environment that we raise our children in to become productive members of society. This love will empower us to build and support our community. This love will comfort and amuse us in our old age.”

Thirty-two in New York: “I just wanna make someone smile. Why is it so hard to find something that is so simple?”

Reading Craigslist, I feel as though I am dipping my cup straight into the swift-flowing stream of human need. Laid-back is the only thing these people aren’t. When I step back onto the “regular” dating sites, I feel like someone coming out of bright sunshine into a darkened room; it takes a while for my eyes to readjust. Everything’s so . . . subtle. On Craigslist, people say what they want; on Nerve or OkCupid, they say who they are, and you infer the rest. Craigslist is scattershot, confessional, desperate, and sleazy. It’s like a wholesale thrift store where nothing is hung up, no two items are alike, and the savviest shoppers wear rubber gloves. The other dating sites are for discerning petit bourgeois who like to read Consumer Reports and make informed decisions. Craigslist’s the insane, open-all-night corner store where you go at 3 am for unhealthy snacks, where a bony cat roams the aisles and there’s a permanent card game going on in back. You go there for what you want right now and will most likely consume in private. Or you go there because you just can’t sleep, and you need somebody else to know it.

Sometimes I wonder how anyone meets anyone in this world at all, the world of cooped-up office buildings and endless choices and constant movings from city to city, the total lack of pushy clans at your back making you do it, and the epidemic of complete and total laid-backness that one encounters in polite society. I worry that online dating has the potential to become an end in itself, an empty activity that soothes in its ability to offer casual, meaningless contact, and the illusion that whenever you wanted to, you could dip into the well and walk off with a partner. I wonder whether that sense of available variety makes it less likely for us to choose, to take something home today. After a while, the thumbnail images and clever sobriquets all blend together, equally desirable, equally “meh.” My California roommate may have been right about this one thing: no one ever stayed together because they had a great “how we met” story, but it doesn’t hurt at first, when you need some kind of glue to bind you to a complete stranger. I feel as though I could wander forever through these halls of pixel, unable to tell one well-traveled, dive bar–loving hopeful from another.

But then I think about Craigslist, about all those howls and barbaric yawps. I think about the needs they express — for sex, for companionship, for the companionship that comes along with sex and the sexuality that we hope for in our companions (and really, I wonder, how big is the difference between just wanting to make someone smile, and wanting to make a sloppy woman experience pure and total ecstasy within?) — and I try to imagine this humming undercurrent of need as the grid, the binary matrix of ones and zeroes that underlies the colorful, orderly, brightly lit spaces of the mainstream online dating world. I like to think of it as the subway under the city: a hidden, propulsive force that eventually moves the best of us to the places we were too laid-back to know we needed to be.