50,000 First Dates: Online Dating Makes Finding a Partner in NYC Harder Than Ever

A major, and ridiculously exhausting, shift in how we mate as a species

Illustrations by Samantha Hahn.
Illustration by Samantha Hahn.

There was a time, not so long ago, when I could look back on my relatively barren romantic life and count, one by one, the half dozen first dates I’d experienced. That was last year, before I casually sauntered into the wide and anarchic world of online dating, overwhelming my senses with the vast number of available women in New York who were willing to meet for drinks or dinner or perhaps an afternoon walk.

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It wasn’t until recently, when I stepped back to reflect on my time in the digital dating arena—a whirlwind of pretty faces and predictable interests and prosaic conversations—that I realized my lifetime date count had, like a strain of mutant amoebae, multiplied by more than sevenfold. But only one date—and I went on close to 50 via online services—made it past the first encounter. That one petered out almost as quickly as the rest.

I certainly didn’t set out to meet as many women as possible, an exhausting goal. I much prefer spending time with old men, who put me at ease; girls frighten me, and I have been known to vomit when the prospect of romance presents itself, fraying my nerves. I was, however, looking for a relationship—long- or short-term, as the online dating argot goes—which, I guess, requires you to do things that make you uncomfortable. 

I am, as the Jerome Kern tune goes, old-fashioned, even though I’m 26, and I like old-fashioned girls. If I could bend the world into another reality, I would mold it after Woody Allen’s great musical comedy Everyone Says I Love You, in which attractive couples dance about the sidewalks singing old jazz standards.

But I can’t, so last summer I joined OkCupid, the online dating site. I’d made an account one sad evening a few years ago, but the process of scrolling through mildly pornographic photos of women I didn’t know felt voyeuristic. I deleted my profile within a week. This time around, however, I was tired of being alone, and the possibility of meeting a lady offline seemed unlikely, even in New York, where women outnumber men—but also especially in New York, where everyone seems so guarded and preoccupied.

I am, as the Jerome Kern tune goes, old-fashioned, even though I’m 26, and I like old-fashioned girls. If I could bend the world into another reality, I would mold it after Woody Allen’s great musical comedy ‘Everyone Says I Love You,’ in which attractive couples dance about the sidewalks singing old jazz standards.

When I’d completed my new online profile, I sent it over to a female friend for vetting. Add an inch to your height, she said, and put a few female writers in your list of favorite authors. I took her advice, making myself 5-foot-11 while adding Nora Ephron, Katie Roiphe and Gail Collins to a list that included E.B. White, Dwight Garner and Tobias Wolff. Then I got to work, sending out messages to a slew of women.

Things started out slowly. A date one month, another the next. A lack of interest on her part, a lack of interest on mine. There were lots of aspiring actors and lots of people in PR, and most of them, I learned from their profiles, were seriously into men who “don’t take themselves too seriously,” which is an idea that I object to. I’m not even sure what it means. Why shouldn’t someone take himself seriously?

As the search continued, I’d come home each night to my computer and spend hours scrolling through the vast sea of faces. After a few months, I’d gotten used to the unwritten rules of messaging—never introduce yourself with a “What’s up?,” among other trivialities—and my date count started to pick up as I ricocheted from one woman to the next. Soon enough, intoxicated by the possibility these services offer, I’d downloaded Tinder, the location-based dating app, and the Jew-finding app JSwipe (“Mazel Tov!” it says when you’ve found a match). That’s when things really started to take off.

Before I knew it, I was going on three or four dates a week. Each one happened at a bar, which is not a bad place for a first date. But it’s also a terrible place, as you are forced to sit and stare at a person you barely know for a long period of time without the option of looking away when awkward silences arise—and they always do. After a while, I got tired of explaining, over and over again, how journalists come up with story ideas—by going on online dates, of course!—and pretending that I like living in Bed-Stuy, so as not to seem too negative. The whole romantic process was starting to feel forced, perfunctory, dehumanizing and, yes, expensive.


My experience, it turns out, isn’t unique. 

“It never felt natural,” said a 28-year-old copywriter (likes Don DeLillo) who lives in Brooklyn and recently deleted his OkCupid and Tinder accounts in favor of offline encounters. “I felt like I was working as a machine, pumping data into a function and hoping to find the right results.” 

“Is it an ongoing interview process?” asked a financier (likes SoulCycle) in his early 30s. “Are we just constantly interviewing people because we can?” 

“I used to think online dating was the best thing to ever come along, but now I think it’s almost a curse,” said a 43-year-old photo editor (really good at: swimming, cartwheels, eating French fries). 

“It’s exhausting having the same conversations every night of the week,” another online dater (enjoys rock climbing) told me.

“I hate the continuous first date,” noted a 30-year-old digital marketer who, in her 12 years of online dating, has been on close to 400 dates. (Hates trashy romance novels.)

I can’t tell you how much time I’ve spent swiping through Tinder, in a state of confused arousal, to find matches—in the bathroom, at work, walking down the street, even on Tinder dates—a sea of names and faces and random pornbots sloshing around in my brain.

This is a major, and ridiculously exhausting, shift in how we mate as a species, the biggest, it seems, since birth control. As online dating becomes less stigmatized—just 21 percent of Internet users think online dating is “desperate,” down eight points since 2005, according to the Pew Research Center—more and more singles, hoping to meet their match, are turning to the digital world. It isn’t the age of the hook-up; it’s the age of the never-ending first date.

While any slut can game the system if he or she so pleases, bedding the city via Tinder or any number of online dating apps, what’s less often acknowledged is that regular people are going on an inordinate number of dates and getting very little—sexual or otherwise—in the process. I’d like to say that this shift implies we’ve become bolder human beings, but that’s sadly not the case. 

The bar is simply much lower than it used to be. Unlike asking someone out in person, you don’t have to muster the strength to walk up to someone, or even just call them, and possibly get rejected. The vulnerability—and the spontaneity that goes along with it—in romantic connection is diminished; online dating may make you a more active dater, but it also turns you into a more passive romancer. Instead of going out with someone you already know you’re attracted to (the old way), online daters now use first dates to find out whether they like someone at all. 

“You really know nothing about a person when you arrange a first date with someone through an online source,” said Harry Reis, a professor of relationship psychology at the University of Rochester. “Imagine if you were to pick names out of the telephone book and go on a first date. How many of those do you think you’d feel a sense of connection with? Probably very, very few.”

This is not to imply that you can’t find your soul mate through an online source. A former colleague of mine got married to a man she met on OkCupid, and there are a number of Tinder success stories. But there are 400,000 OkCupid users in New York City alone, and while I’d like to imagine that they’re all finding love, what’s more likely is that they are just burning themselves out going on date after date.

“It’s an endless buffet table, kind of like all you can eat,” said a 30-year-old art director (level-headed, thoughtful and appreciative) who recently quit OkCupid but still uses Tinder.

“Everybody is a box of cereal,” said another 30-year-old online dater (likes dried organic mango slices, no sulfur), a tech entrepreneur, who jumped into serial courtship last year to get over an ex-girlfriend. He went on as many as six first dates a week for half a year, spending $1,000 a month on his string of first encounters. “I wasn’t looking to make a choice,” he told me, adding that he never asked a girl out again, nor did he try to sleep with any of them. “I was looking for the experience of, ‘Oh, I don’t have to because there’s so much availability out there.’”

So much availability indeed. Sometimes it seems like the supply is a threat to settling down, as are the apps themselves, which, while you’re using them, can feel as consuming as Facebook or Twitter or email. I can’t tell you how much time I’ve spent swiping through Tinder, in a state of confused arousal, to find matches—in the bathroom, at work, walking down the street, even on Tinder dates—a sea of names and faces and random pornbots sloshing around in my brain. Occasionally, I’d see colleagues and acquaintances on OkCupid and wonder, in embarrassment, if they’d seen me, too.

The swiping and the searching is, for the most part, mindless (I would swipe right on almost every girl, just to see who was interested in me—a form of self-validation). On OkCupid, you can pay one dollar for a boost to promote your profile to other users, which I used incessantly, as though it were a slot machine. As my dating mania reached its climax, I also paid $20 for an A-List subscription, which allowed me to view other girls’ profiles without letting them know I’d been looking. (Creepy, right?)

Illustration by Samantha Hahn.

The messages are different. I spent so many hours crafting notes to so many female strangers that I began to worry I might burn myself out as a journalist. But I’d also send the same message to a load of girls on days when I didn’t feel like thinking—sometimes a simple “Howdy,” which my female friends told me was weird—just to see if anything stuck.

That’s what I was doing one afternoon on my phone when I accidentally copied and pasted the URL of a New Yorker piece by Observer alum Nick Paumgarten into the message box on OkCupid and sent it off to an unsuspecting girl.

“Thanks, Nick,” she wrote, impressed by what she took for my writerly prowess. “You have quite a way with words.”

Mortified, I deleted our conversation and hoped she’d never write to me again. (She didn’t—sorry, Nick.)

Perhaps I could have explained to her the humor in the situation and actually gone out with her, but I wasn’t willing to risk embarrassing myself. I like people who appreciate The New Yorker, after all, like the cute 22-year-old paralegal from Florida who told me, on our first date in the Flatiron District this past winter, that I was a “diamond in the rough.” Alas, maybe a little too rough. “You’re great,” she said in a text the next day, when I’d asked her out again. “But I honestly don’t think I could see myself being romantically involved with you.” 

Really? Not even one more date just to see if you were wrong? That’s not what I said to her, of course. I didn’t push it, thanked her for her honest reply, and that was the end of that.

There’d be other girls, I knew, like the 25-year-old social worker (liked jazz(!)) I met at a bar in the East Village. She was great. I would have gone out with her again in a second. She was pretty and calm and comfortable with herself, and she told me, without compunction, that she liked veal. I like girls who like veal. A couple of days later, I asked to see her again. She got back to me right away. “I really enjoyed going out with you,” she said via text, “but I’ve just decided to start seeing someone exclusively.”

Then there was the 28-year-old divorcée (liked craft beer) I met for drinks in Williamsburg in April. Over the course of five hours and many, many pints, we talked about a lot of private stuff—or, more accurately, she did—and by the end of the night we were making out at the bar. “Thanks for being the best part of my weekend,” she said in a text shortly after our date. We’d have to get together again, she told me, when she returned from a week-long trip to the Caribbean. I texted her—not called, of course, because no one does that—when I thought she’d be back and never heard from her again.

Though my immediate instinct was to assume she’d died in a plane crash—why else would she ignore me?—I can’t say I was surprised by her silence, or even disheartened. By that point, I was used to it.


I may, of course, be an unreliable narrator here. Perhaps I was doing wildly inappropriate things on these dates that turned the women off for good—I have a tendency to bring up poop and/or masturbation when I get drunk with my friends, for instance. For the most part, though, if I remember correctly, I mostly just sat there and listened and talked and rubbed my hand nervously through my hair as I sipped beer.

And to hear other online daters describe their worst dates, I was doing O.K., even if I may be “incredibly awkward,” as one Tinder girl I went out with put it to me after I meekly tried to kiss her on a subway platform as her train was arriving.

You never know how people are going to be when you meet them offline. “The things that we find attractive in an online profile,” said Benjamin Karney, a professor of psychology at UCLA, “have almost nothing to do with the things that we find attractive in a real life person when we’re sitting in front of them. What we react to in a person is behavior, but what we see in a profile are attitudes and preferences and background characteristics.”

Also looks, which I am most likely to respond to. Whether I get along with you is another story, and it’s probably not going to be decided—revelation!—by whether we like the same magazines. Interests may point to values, of course, but it takes a while to figure someone out, and a first date may not even offer enough time to do that adequately. 

Judgment also runs so high on a first date—especially one arranged online—that sometimes a dater will dismiss a potential partner when he or she might have been a good match. This happened to a 44-year-old in Chelsea, a former children’s educational game manufacturer who moved to New York a year and a half ago and had been on about 15 dates in two months before she logged off for good recently. She met a man at a bar who, online, had said he worked in securities. Then, on the date, he admitted that he actually worked as a security guard, which was misleading, but seems like a forgivable offense, if you’re into the guy.

“He was dressed so nicely, he was handsome, and I’m sure that he was a really nice person,” she said, “but he just threw me way off and then that was that.”

I’ve been there. I once met a pretty and well-dressed Eugene Lang student at a bar in Union Square who said she liked Anatole Broyard, one of my favorite writers. She pronounced his name A-na-TOL-ee BROY-ard, though, which pissed me off, for some reason.

Still, there are those who find romance after months or years of toiling. “Online dating is work,” said another woman in her 40s (likes Faulkner), an artist. “I just looked at it as sheer labor.” She spent four years in the digital dating trenches—going so far as to use a dating site called OnlyFarmers.com—before she found a man she is happy with about four months ago via OkCupid.

Once I accidentally copied and pasted the URL of a New Yorker piece by Nick Paumgarten into the message box on OkCupid and sent it off to an unsuspecting girl. ‘Thanks, Nick,’ she wrote, impressed by what she took for my writerly prowess. ‘You have quite a way with words.’

“He was a good conversationalist and he told me some pretty private things about his life on the first date,” she said. Now, she added, given her newfound success, “I’m convinced that you have to go on 50 first dates before you meet the person that you like.” Mr. Reis backed up her thesis. “You have to experiment a lot,” he said. “Remember, all it takes is one hit. If you go on 50 first dates and you find one that works, I’d call that a success.”

And then there are the unlucky people, like our digital marketing friend, who has been on nearly 400 dates. “It got to the point,” she said, “that I would forget someone that I had gone out with on one site and then see them on another site and realize that I had already gone out with them.”

The only ones who genuinely seem to enjoy serial courtship are the ones getting laid. “If you’re going to have a negative attitude about it, you’re not going to have fun, and if you’re out there desperately looking for someone, you’re shooting yourself in the foot,” said a 31-year-old Brooklynite who works in renewable energy, goes on about two first dates a week and has a rotation of eight women he sees and sleeps with on a sporadic basis. 

“I was genuinely trying to meet people I’d click with and want to hang out with again,” said an entrepreneur in his 30s. “But,” he told me in a Facebook message, “I ended up having what would probably be considered a ‘high quantity of sex’ (at least according to my GP) as a side effect.”

The trouble is, I’m not that kind of guy. Oh, how I wish I could be a slut, if only for a little while! But I’m shy and insufficiently assertive and quite anxious and have trouble reading women. I did go home with one girl. She was sweet and easy to talk to, but also a bit remote. Over the course of the evening, she alluded several times to going back to her apartment, which surprised me. By the time we did, in a drunken daze, I realized that she had enlisted me in an odd role playing game I didn’t know I was a part of.

At her place, she was by turns seductive and standoffish. She immediately took her pants off. “This is what you wanted, isn’t it?” she said, emerging from the bathroom. Then, as we got into her bed, she seemed to be changing her mind.

I backed off, confused.

“Just go along with it,” she said, breaking character for a moment.

I did, but I also never saw her again.

Over the past few months, I have tried repeatedly to delete my online dating accounts, only to redownload them shortly after. (Who else is going to tend to my 1,200 Tinder matches?) I haven’t been on an online date in about a month, though—I deleted my OkCupid and Tinder and JSwipe accounts a few weeks ago, and I feel like I have three phantom limbs at the moment; I’m hoping that’s just temporary.

I realized that the process of dating serially was becoming, to me, a new and very boring kind of social activity, closing me off to the kinds of offline encounters that would allow me to find someone I might be attracted to.

Last month, right before I quit online dating for, I hope, the last time, I was at a rooftop party in Williamsburg when I met a goodlooking girl who seemed smart and funny and kind and all of those good things. (I hadn’t checked OkCupid or Tinder all night, which was a good sign.) 

We only talked for about five minutes, but there seemed to be something there, and when she left, she glanced back at me with the kind of look that told me I should have asked for her number. I already knew, after all, that I liked her. A few days later, thinking back on the party, I remembered that I’d seen her on Tinder. 

We hadn’t matched. 

50,000 First Dates: Online Dating Makes Finding a Partner in NYC Harder Than Ever