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The New Position on Casual Sex

There's something about the idea of people in the most titillating city in the world -- where walking down the street can be an erotic experience -- looking for sex online that seems somehow wrong. You are upstairs on your computer looking for people to meet; downstairs, everywhere you look, there are people to meet. And the whole thing is a little ass-backward: You're not going to hook up with someone you're not physically attracted to, and you have a much better chance of meeting someone you're attracted to in the big wide world than on the computer, no?

Still, it has its advantages, mostly on the building-confidence front. I'll admit to having spent a few nights in the databases after an explosive breakup with my boyfriend. He had left me for someone else, and I was angry, brokenhearted, frantic to find a light at the end of the tunnel. I answered a few ads posted by guys I thought were particularly hot or funny, but lost my nerve when I looked a little more carefully at one of their photos and realized he was a classmate from Dalton. That wasn't the fantasy I was after.

Plus, the whole enterprise was unsettling, putting me in a constant state of semi-arousal (You mean I could have sex with him? And him? And him?). Men might like that feeling, but it made me nervous. And all that trolling took an immense amount of time, despite the common wisdom that it's the best shortcut around the messy, excruciating experience of finding a mate. Nor do you know more about suitors when you meet them in person -- in fact, you end up talking about all that dumb first-date stuff anyway, because the person sitting across from you is still a stranger, no matter whether you share a favorite onscreen sex scene.

In fact, online dating has its own annoying requirements. There's always something to do, whether it's tweaking a profile to yield the maximum results from the optimal suitors, or updating it constantly to remain at the top of an ever-lengthening list of personals, to say nothing of sifting through the staggering number of responses (at least if you're female; men are still the majority of users). Then you've got to run around and meet these people, and a lot of them are creeps. "It has completely taken over my life," admits Jessica. "But in a good way. You get to be in all these Sex and the City plotlines without ever having to put on shoes that hurt."

There are all the stories you'd expect: the stockbroker who takes women to lunch at Jean Georges and afterwards shopping for a dog bowl with his name on it. A friend of a friend, a Philadelphia businessman, keeps a pied-à-terre in the city for weekends to "enjoy the ease and quantity of New York women," arranging five or six dates through JDate beforehand. A colleague reports: "A couple months ago, this guy I met through Nerve took me to dinner and then we fooled around in the bathroom of a bar and then he exposed himself to me on the subway platform. He thought it was sexy!"

Here I am having these tawdry affairs because I don't want to give men I might want to date the wrong idea by having sex with them, but I don't want to live without sex.

In fact, the online personals could serve as a laboratory for studying people's ideas of what's sexy. "I have ads on all the sites," says a divorced stockbroker in his forties. "Usually, I meet women at Pastis, in my kilt. It's a quick way of separating the wheat from the chaff -- it lets you know immediately that I have my own peccadilloes. And it's oddly masculine in its own way." He recently took home a 20-year-old he met on CraigsList. "She left pretty quick in the morning -- I think she felt buyer's remorse. Oh, well, it was fun for me."

"The first girl I met was Miss J.Crew, a preppy cutie," says Adam, 36. "I was like, 'If this is what online dating is like, bring it on!' She wanted to get together right away, so we met for dinner that Tuesday on Third Avenue. Although I can be pretty sexually adventurous, it was a school night, so I was thinking dinner and back home. But she attacked me! We went back to her place, some phat townhouse in the Seventies. She's got a roommate, and I'm thinking the place is too nice for a roommate situation, but whatever, and the roommate's some old guy, but whatever. He goes upstairs and we have mad sex on the couch. Then I don't hear from her for a year, until she calls to say she owes me an apology -- that 'roommate' was her husband. He gets off on her being with other men."

Truth be told, it's stunning how many married men are dating online (the only more-represented group of men may be those under five nine). Upon soliciting interview subjects for this story, I received a lot of e-mails like this one: "I'm 33, live in midtown, work downtown for a major financial house in risk management, married, no kids. Been cheating almost since I got married. With the various women I've been with, it's ranged from straight vanilla sex to bondage to threesomes to sex toys to making a home movie. So far I've slept with two dozen women, all met through the Internet, with three long-term affairs of at least a year, including a current girlfriend who I see twice a week."

"After a couple months of seeing this guy, I got this weird feeling that he was married," says a friend, "so I started bugging him about it over e-mail and finally he sent me a message without any writing in it, just a photo attachment. It was the same shot he used in his personal, and in that one you could tell he had his arm around someone who'd been cropped out, but now it was intact -- the other person was his wife." But a few weeks ago, she went out with a journalist to the Magnolia Bakery for cupcakes. "We went outside right when it started to pour," she says, "and there we were, cupcakes in our hands, balancing umbrellas, and we just started to kiss, the umbrellas trailing behind us like a sixties movie poster."

The first guy Jessica dated wasn't married, but he was divorced -- they met at MoMA, where he greeted her with a single red rose, but the sex was bad. "Then, the next day, it turned out that the rose was infested with fruit flies. It took me a week to squash them all." Next up was an Emmy winner -- still, "he had confidence issues. Go figure" -- and then Anger Management Guy, who drove her back to Fort Greene at the end of the date, but when they got stopped for speeding and he couldn't talk the officer out of the ticket, he yelled out the window at the policeman's retreating back, "Thanks for nothing, Officer Dickhead!" More recently, there was a dictionary editor who by the second drink had told her about all his heroin-addicted ex-wife, plus how his mother hated him, plus how he was deathly afraid of women who wear high heels. She rolls her eyes: "I mean, TMI" -- too much information.

Just when she was feeling cursed, she met a film projectionist on the Upper West Side who looked like Vin Diesel and was "the best, ahem, built I've ever had." For their first date, she brought him hot chocolate at the theater. "It's so cool in the booth, nothing's digitized, it's like you've gone back 40 years in time," she says. "He had this little schedule in his pocket and ran around from theater to theater changing the reels. Did you know that when they transport those big film canisters they put code names on the outside, to deter thieves? Like Black Hawk Down will be White Eagle Up." After a few months, though, he started to complain that she said whatever popped into her mind without thinking. "When he said it, I said thank you," says Jessica, "because I thought it was a compliment." It wasn't a compliment. This was a discouraging turn of events, but on the train home from work one day, she had an epiphany. Sandwiched between a bunch of people on the downtown A, she started to read a W. H. Auden poem on a "Poetry in Motion" poster:

Looking up at the stars, I know quite well That, for all they care, I can go to hell. But on earth indifference is the least We have to dread from man or beast. How should we like it were stars to burn With a passion for us we could not return? If equal affection cannot be, Let the more loving one be me.

"I was like, 'That's it! That's it!' " says Jessica, who Googled the poem when she got home, printed it out, and stuck it on her fridge. "That's why this online-dating stuff is so great -- it's a way to overcome whatever hurt you have from ex-boyfriends or weird things in your past, a way to refocus on how important it is just to put your love out there. That's what the whole ice-queen thing was about: pretending that I didn't care about what I was getting back from people, even though I cared so much. I don't mean to sound like some lobotomized self-help addict, but for the first time, I no longer feel like I have to pretend."

There's nothing wrong with people feeling less lonely, or having a new sense of optimism about the abounding fish in the sea, or acting on a fantasy that would previously have remained just that. But perhaps it's also made commitment seem a lot less appealing: Never before has the idea of having a girlfriend or boyfriend had less purchase on a generation. Will they commit, ever?

"There is probably a downside -- a more liquid, fast-moving marketplace may cause some people to feel that they can always trade up, and you can make a case that endless options are the enemy of contentment," says Griscom. "This is the quote-unquote late-capitalist existential crisis. Well, you can reminisce about the good old days when you lived on the family farm and married your cousin. Sure, life is simpler and more stable when people have very few options. I'll take the present."

Jessica, in any case, has finally found someone she likes. He's a law student who likes her confidence but also accepts the goofy, silly part underneath. "Honestly, I never thought it would happen," says Jessica. "I always thought I was too high-energy or too selfish or too crazy to settle down. But now I think I just never found the right person, because there's no substitute for someone constant, someone to say 'Hi, honey, how was your day?' or 'I love you' every night." A few days ago, she "hid" her online profile, so she's not receiving any more responses from guys at the moment. "Yeah, I'm off the junk," she says. "At least for now."