8 Keys To 20-Something Dating In New York City

When Harry Met Sally
When Harry Met Sally

1. Talk about how hard it is to date in New York City

Since New York City is one of the most populous cities in the world (with approximately 44 trillion guys wearing blue J Crew shirts), it’s also a city where you’ll fall victim to constantly being compared to superior options. For everything he has to offer, there’s another guy named Logan who’s the heir to an oil company. For everything she has to offer, there’s a model who’s too attractive to legitimately exist anywhere outside the confines of Houston and Spring St.

Dating in New York City is a lot like choosing a movie to watch on Netflix, except that you’re Blades of Glory and every other movie was nominated four 4 Oscars.

2. Be passionate about transportation routes

This holds true no matter your place in the “20-something” game. When you’re younger, the prospect of having a commute gives the whole thing a wide-eyed first day of school feel. When you’re a little bit older, your knowledge and city cred means that you could suggest efficient transportation routes in your sleep:

“Take the crosstown bus, eat a taco, and then hop on the 1…make sure to eat that taco, I’ll lunch suggestion-terrorize you until you do.”

3. Talk about how broke you are, but somehow have enough money for a $17 Prosciutto sandwich.

Of course, everyone knows that a $17 Proscuitto sandwich is an untenable expectation for all involved — especially given the meager size of the sandwich, and the glaring lack of balsamic. They said drenched, and this clearly isn’t drenched.

Alas, the higher spending that goes hand and hand with initial courtship is certainly amplified here in the Big, It-Costs-$10-For-A-Granny-Smith Apple. No matter whether or not you split the check, old-style dating — in which you eat pasta with white clam sauce and some guy with an organ sings to you romantically — is increasingly unaffordable.

4. Do cliche “Real New Yorker” things

Basically, eat cheap dumplings in Chinatown instead of hitting up the Museum of Natural History. Ride bikes in Prospect Park instead of slowly disintegrating in Times Square.

Doing the most cliche “Real New Yorker” things you possibly can is important, because it implies that you, as a team, are conquering this city.

5. Remember that you’re the weird one who’s obsessed with your industry

The thing about New York City is that there are about $17,000 New York Cities within New York City. You’ve got everything from the finance world, to the struggling musicians world, to the Rounders-esque underground poker playing world. Naturally, everyone competes and exists within their respective world, and oftentimes forgets that people outside their realm are too busy immersed in their own orbit to remotely care about what’s going on in your galaxy.


So if there’s some sort of crazy scandal in the advertising industry that profoundly affects the way you operate, it’s highly unlikely that anyone outside your silo will even be aware of the scandal. When dating someone outside your “world,” — especially at first — remember to be slow and deliberate; ease them into the alarming reality that is your NYC.

6. When talking about your #grind, be results oriented

New York is known for its grizzled, shut up and let your game speak attitude. There are other cities more focused on having a lot of exciting “projects” amidst 90 minute lunches, but NYC is most certainly a place in which you need to walk the walk.

So if you’re gonna spend the whole date bragging about your awesome startup, actually talk about what you’ve been doing with your awesome startup. Everyone has an awesome startup. Be exceptional.

7. Beware of the long distance relationship

Obvious, but needs to be said. If you have to transfer more than once to get to his or her apartment, there’s little point in even trying. Unless of course, the person in question lives in TriBeCa.

8. Just have fun out there

Not to sound like a Little League coach who realizes his team is severely lacking in talent, but no matter your sitch just try and make it as entertaining as possible — whether it’s dating, an aspirational career, or pizza sampling. just try and have fun out there. You’re here, so you might as well leave with an entertaining story or 4,000. Thought Catalog Logo Mark

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