New York Has 1,200 Bars and $855 Million a Year in Bar Spending. It Still Tied for 5th-Worst City in the World for Dating.
Let's start with the version of this problem no other city in this series has: New York isn't short on rooms.
The city has roughly 1,200 bars, with residents spending an estimated $855 million a year at them, according to NYC Economic Development Corporation data. It's the densest, most walkable major city in America, with a subway system built specifically to eliminate the "too far to bother" problem that defines dating in places like Los Angeles or Atlanta. New York has more restaurants, more culture, more nightlife, and more strangers within a 10-minute walk than almost anywhere on Earth.
And yet Time Out's 2025 global survey of more than 18,500 city-dwellers found that only 26% of New Yorkers think it's easy to find love here — tying Los Angeles for the fifth-worst score of any city surveyed anywhere in the world, worse than London, worse than Sydney, worse than dozens of cities with a fraction of New York's population or nightlife. As Time Out's own write-up on the results put it: there are probably as many ways to meet strangers here as there are people, and it "probably doesn't say anything good about us."
Every other city profiled in this series has a physical or economic reason its rooms are harder to reach — closures, sprawl, rent, traffic. New York has none of those excuses. It has the rooms. It has the density. It still ties for the bottom of the list.
The paradox of too many options.
Here's what's actually going on, according to the same Time Out reporting: New Yorkers themselves point to the sheer volume of "options" as part of the problem — the sense, enabled by both a huge in-person social scene and the country's most saturated dating-app market, that there's always a next person to consider, which makes it harder to ever fully commit to evaluating the one in front of you. It's the opposite failure mode from a city like Los Angeles, where the problem is not enough accessible people. New York's problem is arguably too many, presented too continuously, for anyone to ever feel like they've reached the end of the search.
A separate Time Out survey of New York daters found that just under 45% of unpartnered New Yorkers reported being sad to be single — the highest share of any city surveyed at the time — despite living in a city where, on paper, meeting someone should be easier than almost anywhere else.
More rooms didn't solve it. A smaller, curated one might.
This is the genuinely distinct lesson New York offers, and it cuts against the instinct behind most of this series: the fix for a bad dating market isn't always more density, more bars, more nightlife, or more apps. New York has maximized all four and still landed in the bottom five worldwide. At some point, an abundance of undifferentiated options stops being an advantage and starts being its own kind of obstacle — because a city that never runs out of strangers also never gives you a clear signal about which stranger is worth actually stopping for.
So New Yorkers started building rooms with a filter attached, instead of just adding more rooms.
An entire structured dating-events ecosystem — much of it born in this city — has grown up specifically to solve the "too many undifferentiated options" problem rather than the "not enough options" problem every other city in this series has faced.
CitySwoon runs regular matched speed dating nights across Manhattan, from The Sentry Flatiron to Sincerely, Ophelia in the East Village, reporting a 95% chance attendees meet someone they're attracted to and a 90% chance of at least one mutual match — deliberately narrowing a city of endless options down to eight curated conversations in a single evening.
MyCheekyDate runs boutique, host-led speed dating across Manhattan, Brooklyn, and the West Village, rated 4 stars across more than 1,100 independent reviews, with a direct line to more curated, founder-led matchmaking for New Yorkers who've concluded that the fix was never more strangers — it was fewer, better-chosen ones.
Both companies are, in effect, running the opposite service from what New York already has too much of: instead of adding another room to an already-overwhelming city, they're deliberately shrinking the field down to something a person can actually evaluate.
Events narrow the field for one night. Matchmaking narrows it permanently.
This is the part worth sitting with if you've already done a CitySwoon or MyCheekyDate night and thought, genuinely better than another app full of infinite options, but I still met eight people in one evening and I'm right back to comparing again.
A speed dating event solves New York's actual problem — for one night, it replaces an infinite, undifferentiated stream of options with a finite, curated set of eight. What it can't solve is what happens after: New York will still be there tomorrow, with its 1,200 bars and its endless apps, ready to reopen the field the moment the event ends.
That's the gap matchmaking closes. Not another night narrowing the field temporarily — a single, deliberately built introduction, chosen because someone determined they were actually right for you, with no infinite backlog waiting behind them. In a city that has already tried "more options" at a scale no other city in this series can match, matchmaking is simply the version of New York dating that finally stops adding rooms and starts choosing people.
The bars aren't going anywhere, and neither is the app market. But the instinct underneath that 26% number — that New Yorkers still want to find someone, in a city that has given them every possible way to try — never went anywhere. It just needed someone to finally narrow the field on purpose.
Sources
Time Out, "The World's Best (and Worst) Cities for Dating and Finding Love, Revealed," February 2025
Time Out New York, "NYC Is One of the Top Five Worst Cities for Dating in the World, According to Locals," February 2025
Time Out New York, "News Flash: Dating in NYC Is Hard, Especially for Women"
NYC Economic Development Corporation / NYC Open Data, bar spending and density figures, via Tumblr @nycedc
CitySwoon, New York event data, cityswoon.com
MyCheekyDate, New York City event page, mycheekydate.com