Dating in New York Is Miserable. Here’s How to Fix It.

Dating in New York, when you think about it, should be remarkably easy. There’s a huge population of young, attractive, single people, and because we choose to live in a city where your average studio apartment is smaller than a suburban coat closet, New Yorkers spend an inordinate amount of time out of our homes. Unless you’re a shut in (or live in Staten Island), it’s almost impossible to walk outside for more than a few minutes without running into people — many of whom are young, attractive, and single.

But it’s even easier than that. Those unwilling to simply leave things up to chance can avail themselves of a multitude of online dating apps, providing an endless pool of would-be suitors. If dating is simply a numbers game — as I’ve been told on many occasions — the numbers should be in our favor.

And yet just about everyone I know in New York who is single in their thirties finds dating here to be a miserable, frustrating, and dehumanizing chore. Dating has never been easier. But it’s also never been worse.

What’s gone wrong?

First, there are the basic challenges of living in a place like New York. Busy professionals in their thirties usually date other busy professionals in their thirties who, as it turns out, are extremely busy. Set aside compatibility and chemistry — simply occupying the same place at the same time can be an insurmountable challenge. If you’re lucky, you click with someone who lives in your neighborhood, or even your borough. But for people who live on the opposite side of the city, meeting up is harder than getting an audience with the Pope. Opportunities to go on dates compete with late meetings, yoga classes, out-of-town visitors, friends’ birthdays, and trips away from the city. Often the only time people have free are weekday evenings, when, after a long workday and uncomfortable commute, the last thing anyone wants to do is get dressed up just to make stilted conversation with a stranger. And even when you’ve managed to string together a few successful dates with someone, an ill-timed business trip or unusually demanding work project will invariably stall the momentum.

But the problem with dating goes beyond mere inconvenience. The bigger issue is quite simple: There are too many people to choose from. This idea — which psychologists refer to as “the paradox of choice” — is hardly unique to dating. Think of eating: When you go to a fancy gastropub with five items on the menu, you choose something to eat without difficulty — even if you’re not that crazy about any of the options. But at your local diner, where the menu is as long as War and Peace and full of familiar comfort foods, you agonize like it’s the hardest decision of your life.

Dating is much the same way. In smaller cities, or in environments where meeting people is difficult, online dating resembles rolling the dice on a menu item that may not initially be very promising. Often you’ll strike out — but when you do find something interesting, there’s a built-in incentive to see it through; after all, there may not be a desirable alternative so readily available. But in a place like New York, there is an almost unlimited number of people who satisfy your basic requirements — but committing to one when there are so many left to sample is torturous.

Maybe these problems are due to the fact that the entire premise of online dating is absurd. Think about it: You agree to meet a complete stranger and, unless you’re clearly just looking for sex, you’re trying to figure out if you want to spend the rest of your life with them—based on a few awkward hours where you’re both trying to showcase your best self in an artificial environment. Rather than being a relaxing and enjoyable evening with an attractive person, online dates instead resemble an elaborate chess match in which thinking seven moves ahead is integral to survival. You scrutinize outfits, gestures, facial expressions, references, and mannerisms with the intensity of a forensic scientist, hoping to detect signs of compatibility. A misfired joke or tedious anecdote — quirks we might find charming in a friend or relative — become deal breakers. And as we engage in this exercise, we are likewise aware that we’re being watched in precisely the same way, making us extremely conscious of our own behavior. The whole ritual is exhausting, and hardly a good way to figure out if you actually like a person.

Why do we subject ourselves to this ordeal? In part because we’re part of a culture that romanticizes the notion of love at first sight — and one that, in love and in business, stresses the importance of first impressions. There’s certainly something to be said about those wonderful, fleeting moments when you find yourself attracted to a stranger. But think about your life: How many of your most cherished friends are ones you didn’t at first love? How often do we initially consider someone unattractive only to find, after extended exposure to their whole person, that they’re beautiful and wonderful and worthy of adoration? If we chose friends the way we choose dates, we’d have dismissed most of ours with the left flick of a thumb.

And that’s the problem with online dating: We select people from the internet that we don’t know based on a set of criteria that are more arbitrary than we’d probably like to admit. And when we do, somehow, match with people and persuade them to meet us for a date, we discard them within a matter of hours unless their compatibility is immediately obvious, even though our standards are virtually impossible to assess properly in so little time. Oblivious to the absurdity of this whole ritual, we then retreat to our phones and dive in again: the careful curation of photos, the writing and rewriting of our profiles like they’re sacred texts, the messaging, the waiting, the doubt, and all else. And because our culture also prizes conformity and adapts slowly to changing patterns of school and work, we convince ourselves that, in the ostensible prime of our adulthoods, we’re unwanted, damaged, and destined to live out our days alone.

So what can a reasonable person do? One option is simply to withdraw from the whole charade, delete all the apps, and try to meet people the old-fashioned way (or not). But that still doesn’t get around the awkwardness, pressure, and misplaced expectations that are intrinsic to all forms of dating.

Maybe what we need, instead, is to think of dating, love, and romance in a different way. Rather than analyze every aspect of a stranger’s behavior in an attempt to evaluate them for long-term compatibility, we should simply relax and let them be themselves, while doing the same. And maybe, when the first date inevitably ends with a polite kiss on the cheek and a vague promise to get together again, we should actually follow through. After all, the purpose of dating couldn’t be more simple: it’s simply to get to know someone better. Instead of finding an excuse not to.