20 Qs on 20s: Question 2, on dating in New York

by ninameetscafe

This is a series of interviews with friends between 20 and 29 years of age. The aim of this series is not to capture anyone’s individual identity, but rather to glimpse the bigger beyond of what it’s kinda, generally like to be a “twentysomething” these days. I’m attempting a word-based pointillism.

Question 2: Great. You’re a woman in your 20s in New York City. What is great and/or what do you hate about dating in this city?


As a 28-year-old who has never really been into serial dating, New York City is completely overwhelming. Yes, I do get more attention in public places, I suppose because of my “exotic” looks, as they’ve been described: I’m half Mexican, half Lebanese, but have been attributed to all ethnicities except those two. However, that hasn’t implied more dates or developed into truly meaningful relationships.

Quick disclaimer: I’m not looking to date. I’m old-fashioned in the sense that I enjoy getting to know a man in a day-to-day basis (yes, guy friends, classmates and coworkers are in my very short list of “exes”). I often feel that when I’m on a first date, set up with anticipation, I’m not entirely myself–I’m on a “be likable” mode, which urges me to overthink my actions, clothes, movements and conversation. So I turn awkward and uncomfortable and make a mess.

Nonetheless, I have dated in New York. It came out of nowhere (a really good party in Brooklyn), turned into a date (the worst one ever), mysteriously turned into a second, third and fourth date (he was an unapologetic narcissist, though very fun and charming), and we ended up dating for a whole two months. It was a good experience that ended as fast as it started. Yes, it hurt in the end, but I kept telling myself that there are other fish in the New York ocean. I guess that is what I like and hate at the same time: NYC is supposedly so full of opportunities and options to date that it is common to find yourself secretly yearning for your current relationship to be over so you can begin the next one with that cute guy that is checking you out in the D train or with whom you’ve been talking via Hinge. That sounds terrible, but in many ways it is true. I’ve never realized how many people actually have a dating calendar/plan of action/dating apps lined up. It seems to me that it is more like a rite of passage of being in your 20s in New York City, a big part of the social life, a thing to talk about during brunch. Dates in NYC landmarks are definitely fun, but they’re not for me.

(Mexican insert in Brooklyn’s South Slope. Studying my master’s and working by day, watching cooking shows and Game of Thrones by night. I might or might not have a problem watching things being chopped.)


From Cleveland, Ohio, I took the Megabus back to New York City after spending Christmas with family. Ready, set, queue. While waiting for the bus to depart, a John Mayer lookalike walked in. He also took the bus back to New York; at the 7th Ave. and 27th St. stop we went our separate ways. After running some errands in the city, I got on the C train to head home in Brooklyn. Lo and behold, a couple of stops into my ride, my John Mayer walked into the same car! Our eyes met, he did a double take, and then he sat next to me. I kept “reading” as I noticed his glances to check out my book.

In that moment, and in the moments after he got off the train and looked back at me, I wondered what it takes for two people to “make a move” in a city of opportunity. I could’ve said, “Didn’t you ride back from Ohio?” He, “What book are you reading?” Instead we sat there minding our own business. Amid millions of people and countless encounters, it’s easy to take serendipity for granted and default to being passive in dating. Having sooo many fish in my sea hasn’t allowed me to date more. Rather, it requires me more convincing to decide a person is worth my effort.

On top of that, it’s hard to determine what role I want to play in dating as a modern woman. “If I’m a strong, independent woman, does that mean I don’t need a man? Or simply that I should be making the first move?” As a woman in her 20s, at this point in history, I find dating complex, full of uncertainties and requiring a lot of guts. What I appreciate about dating in New York is that it confronts me to figure out my role through unexpected happenstances–love it or hate it.

(I recently celebrated the turn of my mid-twenties, and my first year in New York City. I grew up in Korea and Canada, and have lived in the Midwest, West and East Coasts. I studied architecture and currently work for a city agency as a design project manager. Museums and my church are my happy places. One of my New Year resolutions is to date more.)


Dating in New York as a woman is a very interesting experience, especially, or maybe completely, because of the fact that I am British and have only lived here a year. I am used to cities where there are many more men, who are still single late in their 20s and 30s and where the man is generally expected to initiate all courtship.

In New York, not only do the women outnumber the straight men at some huge proportion, but people seem to be married younger here. This means that for a woman in her late 20s–especially a Christian woman–the pool of eligible single men is pretty small, and those there are tend to be hunted to extinction by terrifyingly aggressive New York women. Pair this with my unfamiliarity of how to chat up men, and my inability to express my feelings with any man that I date, and it is no surprise that I have had a series of somewhat failed experiments with men this past year: all younger than me, unable to express their feelings due to immaturity, but also tolerant of my inability to, and generally only dating me because I am exotic (as much as a pale English woman in New York can be).

So, I either continue to pursue, with lackluster, men in their early 20s who find me an attractive oddity, or I become a bitter New York woman in her late 20s who hates men. Let me explain: living in New York makes you expect the best in every aspect of your life. And my female friends expect, despite experience, the men they take the time to date to be the best of the best. Unfortunately, this leads to many failed dates with men who are generally shorter than them and less educated than them, and as a result probably also intimidated by these impressive, polished women. Unfortunately, to stave off embarrassment at being still single, women mask this with bitterness, before settling into an unhappy commitment to being “single forever.”

On reflection, I think I’ll stick to dating young men.

(I am a newly turned 28-year-old Brit who has lived in New York for 15 months and in Brooklyn for a year. I moved for work from London, where I lived for four years, also moaning about the lack of eligible men. I love New York in many ways, while finding New Yorkers one of the most intractable and rude people on earth–a view I’m sure I share with most of the rest of America.)


My views on dating are pretty alienating for a 24-year-old girl. It is very uncool to tell people you love dating in New York. It’s much more acceptable to vent to your friends about the guy who stopped texting you back just when you thought maybe he’d finally stay in your bed past 3 a.m.

I honestly think New York is the best place to date. And before I continue, I want to clarify that when I say “date” I mean date and I don’t mean fall in love. If you’re looking for your soulmate, then best of luck to you no matter where you live. But, if you’re looking for some good-looking strangers to spend a few fun evenings with, then New York city is where it’s at.

There is an endless slew of people willing to go on a first date, and with things like Tinder and whatever other dating app that just got invented in the last five minutes, it’s so easy to connect with those people. Sometimes you go out, have a great time, and decide to try it again. Sometimes you go out, think the person across the table from you is a total weirdo, and then you can call your friend and laugh about it.

I get that it totally sucks when that guy who may or may not be a psychopath (but made you laugh and always insisted on buying you Doughnut Plant donuts for breakfast) stops texting you back after going on vacation with his best girl friend, but that’s what dating apps are for. There’s always someone else who’s going to be able to grab dinner. And who knows, maybe you’ll accidentally fall in love with one of them on the second date, but–let’s be honest–you probably won’t.

(24-year-old female who likes adult cartoons and tea.)


I’m almost positive that a lot of the dating in New York is happening by total accident. Sure, people are conscious when they decide to exchange numbers, set the day and time, and sit down for dinner. And maybe they are sitting there because they’re both actually emotionally and psychologically secure enough to spend more time in their life considering someone else for the first time (disclaimer: I’m writing about people who are dating as a means to a relationship). But, I really, really wonder. I have a hunch that a lot of people in this town are actually in dire need of good, supportive friends with whom they can be and feel at peace with themselves–not a girl/boyfriend. They need a good set of friends to hear them complain about their boss and/or cry about the late-stage cancer that was just diagnosed in a family member. It’s just that these genuine connections take so freaking long to establish, and, by contrast, the tools for dating have gotten so fabulously efficient at sparking first meetings (if nothing more); it’s ridiculously easy to use dating to meet your short-term social quota and miss the much bigger picture of social needs.

Hm, so maybe what I mean by “accident” is lack of self-awareness. I can’t help but think that, in this city filled with fabulously intelligent, fast-moving people, there are serial daters on the loose everywhere who haven’t dedicated any time to figuring out what kind of companionship they actually need, and are therefore overshooting into the romance field with some new, arbitrary “significant” other in an entanglement beneficial for no one. That frightens me. The idea of ending up as anyone’s arbitrary, quotation-mark-“significant” other deeply scares me, like being used for the wrong purpose, like being that word in a sentence that REALLY should not be there, but it kinda sounds like the right one so it’s tied in anyway. And maybe I’m scared of it especially because I know I’m at risk of it, because hey, individualized attention from a man you’re superficially attracted to feels nice. I’m also scared of it because it seems more likely to happen in a place like New York where many men probably give off an air of self-confidence and self-awareness that maybe isn’t grounded in reality at all. And how long will it take to find out every time?

(25-year-old Christian female: relative latecomer to the dating scene (in New York and anywhere), but also realizing she probably hasn’t been more ready or willing than now to confront the potential ups and downs of it all.)

Resources for further reading:

From the man’s perspective. “Meet the New York Bachelors Who Yearn for Something More” from The New York Times: an article on the midlife men afraid they missed their chance. (“It seems that no single man can make it through his 30s without feeling a pang of regret for the life he could be having, even if it conflicts with his desire to do exactly what he wants all day long.”)

And, “Readers Respond to the Lonesome Single Men of New York.”

Was It a Date?” from The New Yorker: a short video of ladies really, seriously trying to manage the ambiguity.