A Critical (But Highly Sympathetic) Reading of New Yorkers’ Sexual Habits and Anxieties

From left: The Car Salesman in a Relationship With an Older Woman, 32, Brooklyn Heights; The Temporarily Celibate Actress, 23, Astoria; The Single Brooklyn Bartender, 23, Williamsburg; The Mailroom Worker in an On-Again-Off-Again Relationship, 35, Upper West Side.Photo: Joshua Allen; Grooming by Bryan Lynde

So there’s this iPhone app called Grindr. It’s a GPS-enabled social-networking service for gay men. It tells you how many feet away a possible hookup is standing. Each profile comes with a picture, a tagline, the relevant stats, and a declaration of interest. You scroll through a column of heads and torsos arranged in descending order of proximity, tapping on the ones that seem promising and chatting with the ones who want the same things you do. As you make your way through the city, the menu of men reshuffles, and the erotic terrain updates in real time.

Has the search for erotic gratification ever been so efficient? Until recently, being a cad or coquette took a lot of work: You needed to buy a little black book, and you had to go around filling it, and then you had to schedule your calls for a time when the target of your seduction was likely to be at home. The less-self-assured daters in New York faced the sickening anxiety of the first phone call, or the cold approach in the bar. There were palliatives designed to help people cope—the newspaper personal ads, the paid dating services, the dirty videos and magazines—but they were generally understood to be the province of weirdos and losers.

No more. The social technologies that assist in dating and mating today are more than palliatives—they’ve changed the nature of the game. If the cold approach is more than you can deal with, put up a Craigslist ad, or join OkCupid, Manhunt, or Nerve. If the phone call makes you nervous, send a text message. And while you’re at it, send a text message to a half-dozen other people with everyone’s favorite late-night endearment: “where u at?” If nothing works out and you find yourself alone at home again, simply fire up XTube or YouPorn and choose from an endless variety of positions to help you reach a late-night climax.

Virtually everyone under the age of 30 has grown up with their sexuality digitally enhanced, and the rest of us are rapidly forgetting the world before we all were hooked into the same erotically charged network of instantaneously transmitted messages and images. This must be true across the country, but it seems particularly suited for a city as dense, morally libertine, and sexually spirited as New York. Part of the promise of this city has always been that there’s another prospective partner a subway stop away, but not until recently could that partner interrupt your daily business with a cell-phone snapshot of their parted thighs. And of course, the same technology that makes it easier to score also makes the sexual boast or confession easily transmissible to millions of other people.

Every Monday since April 2007, this magazine has posted on its Daily Intel blog a seven-day diary of an anonymous New Yorker’s sex life. It began as an experiment intended to entertain the bored at work, but the candor of the Diarists soon attracted an outsize and devout following. Since October 2007, they have been joined by a rambunctious cacophony of commenters as obsessive on the subject of sex as the Diarists themselves. They criticize, malign, offer support and tips, and digress into arguments about everyone else’s sex lives, as well as their own. The Diaries are often flooded with over 100 comments within 24 hours. Two months ago, the comments on one diary were closed down at 895.

Over the course of the Sex Diaries’ 132-week run, we have seen the city through the eyes of cuckolds and cheaters, sluts and prudes, victimizers and victims, starry-eyed lovers and detached pleasure seekers. We have followed aging women on dismal Craigslist dates, lonely gay men in pursuit of ostensibly curious straight guys, happily polyamorous couples, and co-dependent serial monogamists. We’ve watched some Diarists terrified of succumbing to their feelings and others unable to feel much of anything at all. We’ve watched a black man fly to meet a white couple at a T.G.I. Friday’s in the Midwest and have sex with the wife as the husband watched.

The Diaries can be arousing, a little. But in aggregate, they wound up doing something more interesting: They cracked open a window into the changing structure, rhythm, and rhetoric of sex in New York. The Diarists are a self-selecting group, of course: bizarrely oversharing New Yorkers motivated by the impulse to brag or, as often, the urge to fling their terrible abjection in the face of the world. But as we watched them struggle with the peculiar hazards of mating in New York today (failing spectacularly, or succeeding all too well), we saw that their hassles were everyone’s writ large, and their stories posed a question: Are the digital tools that make it easier to find sex compounding the confusion that accompanies it?

The editors of this magazine asked me to read all 800 pages of the Sex Diaries, and, using them as a source text, develop some kind of taxonomy of contemporary sexual anxieties. (Let others parse Chaucer, my role was that of exegete of “The Polyamorous Paralegal.”) So that’s what I’ve done. Herewith: ten things that seem to be making our playful, amorous youth crazy.

1. The anxiety of too much choice.
A fact so readily apparent that it has escaped reflection: The cell phone has changed the nature of seduction. One carries in one’s pocket, wherever one goes, the means of doing something other than what one is presently doing, or being with someone other than the person one is with. Take this excerpt from a 31-year-old straight male Diarist (“The Transportation Coordinator Seeing Three Partners”) living on the Upper West Side:

12:32 p.m. I get three texts. One from each girl. E wants oral sex and tells me she loves me. A wants to go to a concert in Central Park. Y still wants to cook. This simultaneously excites me—three women want me!—and makes me feel odd.

This is a distinct shift in the way we experience the world, introducing the nagging urge to make each thing we do the single most satisfying thing we could possibly be doing at any moment. In the face of this enormous pressure, many of the Diarists stay home and masturbate.

2. The anxiety of making the wrong choice.
A Diarist with any game at all has unlimited opportunity. A few find this enjoyable and are up to the task: Identify the single best sexual partner available, or at least the person most amenable to their requirements at the moment. They use their cell phone to disaggregate, slice up, and repackage their emotional and physical needs, servicing each with a different partner, and hoping to come out ahead. This can get complicated quickly, however, and can lead to uneasy situations.

An inordinate number of Diarists find themselves at the brink of enjoying one sexual experience, only to receive a phone call or text from another potential suitor. They become a slave to their compulsion and indecision. Consider these snippets in a week of one Diarist, who is deeply conflicted between her Pseudo and Ex:

2:55 p.m. Pseudo G-chats me. Looks like he might be interested in hanging out tonight after all. 9:30 p.m. Meet up with Ex and friends at bar. Text Pseudo to see if he’s up for doing anything.

2:20 a.m. At a bar with Pseudo and other friends. Ex drunk-texts me: “Wanna fuck?” 3:17 a.m. Half-bottle of wine plus mucho beer plus a few rounds of shots leads to me texting Pseudo, “Let’s get out of here and go back to my place.” 3:18 a.m. Pseudo texts back, “I don’t feel like dealing with you.”

11:45 p.m. At a bar with Pseudo. Ex drunk-texts me.

1:30 p.m. Ex calls and wakes me up. Says he needs to talk in person. 7:49 p.m. Text Pseudo and tell him about convo with Ex. Pseudo replies that he’s sorry, he hopes I end up getting what I want. What the hell does that mean? I have no idea what I want, clearly.

This compulsive toggling between options winds up inflicting the very damage it was designed to protect against.

3. The anxiety of not being chosen.
Among active Diarists, the worry that they will make the wrong choice is surpassed by the fear that they might find themselves without one. To guard against this disaster, everybody is on somebody’s back burner, and everybody has a back burner of their own, which they maintain through open-ended texts, sporadic Facebook messages, G-chats, IM’s, and terse e-mails. The Diarists appear to do this regardless of whether or not they are in a committed, or even a contractually sealed, relationship.

12:22 a.m. Tell him I want him. Clothes off, oral sex given and received.

12:45 a.m. IM sound from my computer. I’m currently busy, but I have a feeling who it is at this hour. Continue deliciously illicit activities which turn into both intercourse and mutual masturbation.

1:50 a.m. After we finish, check IM. I was spot-on; it is Mr. 34. And we all know what 2 a.m. IM’s mean.

Sometimes being relegated to the back burner is a sign of uninterest: the late-night booty call, the option of last resort. As often, it is a place to confine anyone who might become emotionally dangerous. The back burner is a confusing, destabilizing, and exhausting place to be, and yet none of the Diarists—even ones who appear sexually sated—appear to view it as anything but a fact of life. It is clearly less terrifying than the alternative, which is to not be on anyone’s.

4. The anxiety of appearing overly enthusiastic.
The back burner is a game, and while the Diarists have various ideas about what constitutes winning, they all agree on how you lose: by betraying a level of emotional enthusiasm unmatched by the other party. Everyone’s afraid disarmament won’t be mutual.

To disarm unilaterally is a strategic error on so many levels—it commits you to a degree of openness you might not be able to maintain, and it exposes vulnerabilities that your counterparty might not be able to resist exploiting. It signals desperation, clinginess, high-maintenance. Most of all, it risks exposing the fond hope, better kept to oneself, that one yearns to leave behind the serial fuck buddies, friends with benefits, and other back-burner relationships to which one had, at some significant expenditure of effort, inured oneself.

The goal of any Diarist playing the game, therefore, is to withhold one’s own expectations until one understands what is expected by the other party. These negotiations require supreme discipline. If you betray the wrong kind of avidity at the wrong moment, your counterparty will not hesitate to pitch you into the shark tank:

3:30 a.m. I text Mike … that I had a good time and would really like to hang out. Ten minutes later he texts me back saying the he would “be down” for hanging out and that we should do it on a weeknight when things aren’t crazy with the parties. I text him back saying he is confusing. He asks how. I felt daring and told him because I can never tell what he want from me. I haven’t heard from him since.

The Diaries are filled with these kinds of casualties and near misses. (“I love this man,” thinks one Diarist mid-coitus. “Mental anxiety attack when I realize I almost said this out loud.”) The commenters have no sympathy for these emotional miscalculations. This, by contrast, from one of the most well-received Diaries (“The TV Producer Who Knows Everyone”) that ever ran:

3 p.m. Already received two texts and countless Facebook IM’s from the Brit. Am slowly starting to realize I have a Stage Five Clinger on my hands. He asks me to hang out again this coming Sunday. I do not respond.

This Diary contained all of the elements that commenters favored: lots of action, multiple partners, emotional fickleness, bad judgment brashly flaunted, and tasty little morsels of private pain offered up in a drolly ingratiating tone.

5. The anxiety of appearing delusional.
The quality in a Sex Diary most admired by commenters is the kind of confidence (or masochism) that allows for ruthless candor. The commenters, it should be said, are a community unto themselves: part intimate support group, part vengeful gathering of Maoist Red Guards. Friends and underminers both, they make it clear that they are not just looking for masturbation material. They celebrate Diarists who exhibit the virtue of self-knowledge, and descend on those oblivious to their own weakness.

The Diarists seemed to recognize this, and over the years the journals have become increasingly reflective, with observational riffs and little bits of self-analysis. One Diarist calls herself “the most emotionally detached woman in the history of New York.” “I should probably be in therapy,” says another Diarist, “but instead I’m just hedonistic, and don’t let anyone get close. I know it’s all a power play.”

These are statements of psychological awareness, but they are also performances. They mask a deeper fear: that one might not be in complete control of one’s appearance. The Diarists cannot bear being judged without having let us know they have properly anticipated it.

6. The anxiety of appearing overly sincere.
Though the Diarists flaunt their emotional honesty, much of what they confess to concerns their terror of losing control. And there is no more efficient way to relinquish control than a sincere avowal of emotion.

The Diarists with the most active auctions use cutesy neologisms to assign categories to the multitude confronting them. One Diarist has three prospects: “the Ex-Boyfriend’s Friend (XBFF), the Art Director, and potentially the Love of My Life.” She’s hoping of the XBFF that “we can maybe talk about a possible long-distance pseudo-relationship.” (And she has been avoiding calling the potential LOML.) Another sends a cell-phone pic of her cleavage to “Band Dude” on day two of her Diary, but later that week finds herself in bed with the “Pseudo-Ex.”

The funny little names make for easy reading—they protect identities, and help us readers keep up with the narrative convolutions. But they also perform an important conceptual labor, subtly ironizing the ones about whom one might conceivably have feelings and neatly dismissing those labeled as a means to an end. There is a certain pride in understanding the limits of a transaction, and installing oneself in the safe position of narrator. This is particularly true for the female Diarists eager to portray themselves just as capable of using others as any man.

You could argue that this playing-to-the-audience is a product of unique circumstances—the Sex Diaries are written for a readership, of course—but postgame narration and color commentary, like rigorous self-analysis, are a constant element of New York mating. Sometimes it feels like the principal reason we have friends.

7. The anxiety of appearing prudish.
The Diarists are eager to show themselves to have conquered modesty—as if anyone is still insisting they be modest. This is particularly true of the young women—and the Diaries are full of them—who operate at the weird place where male pornographic fantasies and their own fantasies of self-empowered pleasure converge:

11:39 p.m. Dance with a couple of my girlfriends. We spot some cute guys in the corner checking us out. Decide to give the guys a show and lock lips with one another. Watch guys’ jaws drop to the floor.

As for pornography, it plays a role in an extraordinary number of Diaries. Still, few Diarists of either sex are willing to betray any discomfort with it, per se. (“See, I have no issue with porn,” one Diarist assures us when discussing his friend’s enormous collection.) Instead they worry about everything related to porn. Its price, for instance. Or a partner’s overindulgence. Occasionally they do fear that the consumption of it may be wearing them out. This, it seems, is incontestable. The experiences of the lonely and the overstimulated by too much sex converge in weirdly affecting moments of intimacy. Picture the montage—a series of apartments in the soft, gray light of dawn:

10 p.m. Contemplate masturbating, pass out before I can summon the strength to find my vibrator.

3:01 a.m. Attempt to masturbate. Pass out with the vibrator still going.

3:30 a.m. Wake up with porn on my laptop and cock in hand. I guess I was really tired.

8. Internet-enabled agoraphobia
For some Diarists, online dating has become not just a supplement to their social lives, but a replacement for it. They prefer to game out all the angles of each prospective seduction ahead of time—to “control the environment and the message,” as one Diarist puts it—and regard the social world itself as “asinine bullshit/social Kabuki.”

The most practiced online daters have mastered the paradoxical etiquette of meeting strangers online and attaining swift mutual satisfaction:

11 a.m. I come across an ad from a sincere-looking South Asian fellow and respond. The fellow responds with a number. I call and we agree to hook up for drinks.

6:17 p.m. The fellow and I do a 69.

Simple. But a certain callousness toward the merchandise is an unavoidable side effect of entering a marketplace as both buyer and seller. If any of the Diarists have felt the sting of disappointment in finding an Internet correspondence go dead, they are immune to it now. They refer to online solicitations as if they were bidders on eBay, and browse potential options without the slightest titillation:

2:30 p.m. Cruise Manhunt, Craigslist, and Adam4Adam in a desultory manner. I’m not really horny. It’s kinda like picking up takeout menus from neighborhood restaurants. I just want to know what’s available.

The loneliest Diarists, seeking a respite from their loneliness, often find people even lonelier than themselves:

1 p.m. Kick off my weekly Sunday-afternoon tradition: “Find Steve on Craigslist.” Steve is a disgusting person I slept with back in April, who attributed my lack of an orgasm to his use of a hair-replacement product. Every Sunday, sure as the rising sun, he posts an ad where he comments about the weather and requests a “beautiful companion” to go to the beach/take a walk in the park/get a coffee/see a movie. He sickens me.

9. Separation anxiety
Collecting all of your friends onto a single page, as all social-networking sites do, alters the way you think about experiences. Formerly, you met people, did things with them, and selected a handful to carry forward into later stages of life. Life was a linear sequence of relationships that began and ended.

But just as Facebook has become an instrument for meeting and seducing new people, it is now also an archive of people you had once seduced or been seduced by:

2:30 p.m. Trying to put off my homework even more, I scan through my Facebook account, my BlackBerry, and my in-box trying to think if I am friends with any guys who I haven’t hooked up with already. Zilch.

And just as the new technologies keep reminding us of the existence of these old relationships, so they make the temptation to relationship recidivism irresistible to many of the Diarists. It seems as if half of the Diarists are either texting or being texted by old flames:

10:30 p.m. He has not called me back, I’m frustrated. Though we broke up a year ago, we usually see each other quite often; however it’s not clear if he is my boyfriend once again. I’m still in love with him. … Don’t want to pressure him, because it’s the reason we broke up in the first place. I begin to think, What do I do to keep him interested and wanting only me?

Maintaining enough distance to permit a decisive break now requires more discipline than many people can muster, and a familiar category of relationship has become more widespread: those that one can never wholly embrace, but never finally refuse. This is wireless co-dependency, and the recovery movement potent enough to cure it (without insisting that its members unplug from the grid) has yet to come into being.

10. The anxiety of being unable to love.
And yet perhaps the most surprising psychological attribute of the Diarists, despite weeks upon weeks of guarding their vulnerabilities from the brutality of the marketplace, is their romanticism. True love! Who could say these words in public without acute embarrassment? It is nonetheless something that the Diarists keep referencing, despite the impression they convey that it is an ever-receding ideal. It’s an odd, negative sort of tribute—a vague longing for something all but lost, but perhaps worth clinging to nonetheless.

10 p.m. I want to love her. And I should. I just, well, don’t. She’s the best girlfriend anyone could ever hope to have. I wish that were enough to love her.

Reading the Sex Diaries all in one enormous gulp, as I have, caused me to surf on the edge of a terrible vertigo as I thought of the many wounds I had myself endured and inflicted during my brief career as a person with a New York City sex life. I had a thought analogous to the one I often have about cars: How is it that we hurtle around the country in these enormous steel boxes and ever survive? And yet people do, sometimes even in the Sex Diaries.

You would have to have read 800 printed pages of them to feel about the following Diary the same way that I did. There was nothing special about it—just an ordinary young man earnestly seeking a happy ending—and it is surely because I endured so much of the heartbreak written into this sprawling document that I make no apologies for the pleasure I took in it, or in disclosing that the somewhat sappy narrative climax contained therein brought me—in my own high esteem, as disenchanted a reader as any alive today—to tears in the reading room of the New York Public Library:

11:15 a.m. Co-worker makes comment that I am glowing. I smile, knowing it’s because of new boyfriend. 3 p.m. I write note to Ex explaining how I thought he should know that I am really happy and dating an amazing guy. It finally feels like some closure. 7 p.m. My head is in the clouds, and I forget to bring my sneakers to my dodgeball game. Still we are able to win one game. I catch game-winning ball! 9:35 p.m. Guy from league hits on me. I happily deny him: “Sorry, I just met an amazing guy, and I think I’m in love!” I smile, feeling really good about telling anyone and everybody about how happy I am and how wonderful he is. I cannot wait for our date tomorrow!

A Critical (But Highly Sympathetic) Reading of Ne […]