Call Me
Has Dating in New York Gotten Easier or Harder? 8 New Yorkers Weigh In
01.08.20

It’s highly unlikely that sociologists of yore could have predicted the immense romantic potential of the digit known as the opposable thumb. But for most of the last decade, “swiping” has reigned supreme. Those who do not enjoy their first romantic encounter by way of an app are strictly an exception to the rule, and thus, by the transitive property, the thumb is today’s true arbiter of love.

But for those of us living in cities, sometimes it feels absurd that we’d require a digital interface to make introductions in the midst of millions of living, breathing, sentient beings. And of course, for decades, people didn’t. Thirty, 50, 70 years ago, dating in the city set itself to a different tune: There were phone calls! From landlines! Blind dates! Subway meet-cutes! CBGB’s!

Vintage charm aside, dating back then came with its own set of woes and stock complaints, as explored in popular culture with…some dedication. Which begs the question: Before the emergence of internet courtship, was dating better or worse? To find out, using the always fruitful case study of the five boroughs, I reached out to New Yorkers of all ages—among them, a Grindr-fluent high school student, a 92-year-old former nun, and a guy who fears “getting me-tooed”—about the trappings of dating in their heydays. From the best (and worst) parts of dating in their era to their typical date, here’s what they had to say about the nature of looking for love in the Empire State.


The Best Part of Dating…

In the ’50s & ’60s:

“I was in my 20s when I moved back to New York. I had my first job teaching in a private coeducational school in Brooklyn. I was finally free from my strict Catholic family moores. I shared an apartment with a girl who was a social worker at the foundling hospital. It was a fifth-floor walk up and although I had very little money (and none from home) it was a wonderful time for me.

This was really my first experience with serious dating and the freedom from scrutiny made it all the more enjoyable. We held very inexpensive dinner parties in our apartments and cooked spaghetti and drank too much—which was all fun and well. There were no barriers except those one imposed upon oneself. We dated across all sorts of ethnic and racial lines and I was surprised to later read about how very uptight the early 50’s were, because it was not my experience at all. It was a glorious time to be in New York. The war was over and there was a lot of optimism about the future and in my experience very little censure.”
—Marydean D., 92

In the ’70s:

“The best part of dating in NYC was the opportunity to connect with so many interesting, creative people, all of whom I would never have come to know under other circumstances. Actually, that was the reason I came to NYC from Kansas in the first place.”
—Deborah D., 68

In the ’80s:

“In high school, I’d done almost all of my dating at malls. We were always at the mall. It was where we would go on dates. It was where we would go to meet boys. It was where we would go to talk about boys. So when I moved to New York and there weren’t any malls, I was completely thrown off. But at that time, I was in college at NYU, and it was just such fun. We were all so young and so excited about how much freedom we had and we’d all come from these small towns which made everything extra shiny.”
—Kathryn N., 64

In the ’90s:

“I honestly think the ‘90s were the peak era of bars and restaurants and venues in New York. I don’t mean just the Studio 54s of the world—I’m talking about the great dives, and the excellent delis. No better era for dating establishments. Also, you could smoke indoors — which was sexy for all the reasons it was terrible.”
—Ryan T., 49

In the 2000s:

“I LOVE talking to strangers, which makes me a total weirdo in 2019—so it’s a good thing I’m not really on the dating scene anymore. When I was dating, I mostly met women at parties or in bars. I met my spouse playing on a recreational soccer team in Brooklyn, which is honestly a great story and I love to tell it. But I think just before all the apps and online platforms came into prominence, it was great to date because you had the freedom to connect more with people around you without being scared of getting ‘me too-ed’ or coming off as a psycho.”
—Dave K., 35

In the 2010s

“Options! And less gender stereotypes or ‘rules’ about dating of the kind you used to see in women’s magazines. I can’t speak to what dating in other eras was like, but I definitely appreciate that I can be myself on dates now and that I don’t feel pressure to perform in a certain way as a woman. It’s also fun (and terrifying) to have this weird rolodex of options on your phone for those phases when you really want to get out there and meet someone new.”
—Emma W., 26

“I think people are more open. You can have conversations about dead parents, and mental health, and vibrators, and politics, without feeling shame or sheepishness.”
—Lily S., 25

Today:

“My friends and I don’t actually do much dating. Most of what everyone does is, like, hook up. Everyone is more interested in the FWB thing—‘friends with benefits.’ We use apps, obviously. Mostly Tinder and Grindr. The apps are cool because we all go to different schools spread across the city so it’s nice that we don’t just have to date kids who go to our same schools. There are so many people our age who are close by. Also, it’s really easy to find other gay guys online, but sometimes, at school, it’s a lot harder to know how to approach or who wants to be approached or whatever. I guess in other generations there weren’t so many gay guys who were out in high school, but I’m not sure what the numbers are or anything.”
—Nicky D., 17

The Worst Part of Dating…

In the ’50s & ’60s:

“I grew up in a close-knit Catholic family attending a private Catholic school, so dating was certainly limited. At 16, I had a boyfriend called Ned whom I dated when I visited friends in Connecticut. We did a lot of kissing outside of the house where no one could see.

Girls in my situation were not encouraged to be alone with a boy at all, but I managed it somehow and never talked about it. Dances were scheduled by our single-sex schools and they were very uncomfortable, because the girls stood on one side of the room and the boys on the other. The nuns and priests seemed to be everywhere and those affairs were certainly not much fun.

I remember a retreat at my school which was in Suffern, New York. The priest drew two lines on the black board; one was short, about a foot long, and the other was at least three feet long. Pointing to the shorter line, the priest said that this was a boy’s self control. Pointing to the long line, he said that this was a girl’s self control. So if there was any crossing the line (sex was never mentioned), it most certainly was the girl’s fault!”
—Marydean

In the ’70s:
“The dating landscape at the time could be very superficial. It felt like a glamorous time to be young in New York but that could make things feel very surface level. For that reason, unless I was introduced by someone I knew, I avoided meeting people at bars and clubs.”
—Deborah

In the ’80s:

“I was nervous all the time. I didn’t know the city that well so I didn’t know my way around much—and without cell phones that meant that every date, especially if it was a guy I didn’t know, was a bit risky. Plus, I wasn’t very good with boys.”
—Kathryn

In the ’90s:

“I dressed really badly. I think that was really the number one thing standing in my way. I also had four roommates, which isn’t really a turn-on for most people. I mostly frequented gay bars or parties hosted by gay men because it was easiest to guarantee that I would meet a guy who was out of the closet and who I actually enjoyed talking to. Those were also just…the people I really wanted to be around.”
—Ryan

In the 2000s:

“In retrospect, communication was a little bit more up in the air. In my more recent dating life, I did most of my communicating via text. But before everyone texted all the time, we made phone calls. And phone calls, as I’m sure you’re aware, are often more awkward than text messages. I generally found that if I’d gone on a good date, the best MO was to just make another plan—with a time and a place and everything—while on the first date. And then, if either of us changed our minds, we could call to cancel, but we’d definitely start out with a plan in place.

The worst part about that was that this is New York and there are an infinite number of reasons that you’d be late for something. But of course you couldn’t just text and say, the A train is fucked.”
—Dave

In the 2010s:

“There seems to be a general apathy towards dating. I feel like everyone always thinks there’s someone better they could be with, so they let things fizzle out before really getting to know someone (I’m guilty of this myself). Also, this might just be because I’m a straight woman with many straight women friends, but it feels like there are all of these amazing, motivated, talented women all over New York and not enough single men who are in that headspace in their 20s and 30s. I don’t know if it’s because men think they should be sowing their wild oats during this time or what, but I’ve had this conversation with so many people of different genders/sexualities who can’t even name a single, normal, datable straight guy they would recommend to a friend. I don’t know if I blame New York or if it’s a bigger phenomenon?”
—Emma

“50 years ago, you dated to get married. Now the purpose of dating has a much broader, much more complicated purpose. Is it about self-awareness? Is it for sex and pleasure? Is it ultimately for partnership? Dating apps have also changed how we meet people. I hate them, I want to know how someone carries themselves, what their voice sounds like, their gestures. You can’t do any of that via Hinge or Bumble or Tinder. Its impersonal and superficial. Some people have success on them but to me, the banter is like a whole second job.”
—Lily

Today:

“It’s tough to actually meet people at school because of the apps. When you watch movies, all of the flirting and dating stuff happens at school. But I think most people my age aren’t really into finding actual significant others. Especially when I use Grindr, it’s definitely not like that. It’s just like…physical. It’s usually kind of awkward.”
—Nicky

Where and How You Meet People…

In the ’50s and ’60s:

“Most of the people I dated in those years were either from Columbia, where I was working on my masters, or from the Berghoff studio, where I was studying acting.”
—Marydean

In the ’70s:

“I mostly dated people that were introduced to me by mutual friends through my work at Ford Models or acting classes I was taking in the city. I met my first husband, who was a photographer, on a photo shoot. We came from different countries and had very different home and family lives. But in spite of all our differences, we connected immediately. I think the fact that we’d both come so far from home in order to be in NYC was a great starting point. When he passed away seven years later I eventually eased back out into the dating world. Then, in my 30’s, dating again was a very different experience. Of course, I was changed too, but the scene seemed less free, and more guarded, or goal-oriented.
—Deborah

In the ’80s:

“For the most part, just through school.”
—Kathryn

In the ’90s:

“Mostly through friends of friends. I feel like we were always doing something. Someone was in a show and we all had to go, and of course, there was an after party. Or there was a protest, or a meeting, or a friend’s band playing downtown. There were so many social engagements, so there was always the guarantee that you could meet someone new”.
-Ryan

In the 2000s:

“Definitely doing an activity. It’s hard to strike up casual conversations at bars full of strangers, but anytime there’s an activity involved, it’s so much easier. So many bars here do a trivia night or a game party. Shuffleboard is like…the cool thing. I once went to a murder mystery dinner party. Stuff like that makes it really easy to start conversations so you don’t feel like you’re being a total creep when you approach someone.“
—Dave

In the 2010s:

“I feel like it’s a pretty even split for me between mutual friends, bars, and the apps.”
—Emma

“I started a thing with a friend of mine that we call ‘boyfriend Saturdays.’ It’s the anti-dating app. We’d go to parties on Saturdays with the caveat that we each had to meet one new person, be open, be flirty, and then, not focus on dating for the other six nights of the week. The whole thing was in service of self-care, friends, exercise, and so on. It wasn’t fool proof but it made the off-nights more about us and the on-nights more open and social.”
—Lily

Today:

“When I dated girls, I met them at school. But with boys, I use Grindr.”
—Nicky

A Typical Date…

In the ’50s & ’60s:

“We usually finished classes at about 10 or 11 p.m. and spent the rest of the evening together, mostly in local bars.”
—Marydean

In the ’70s:

“We went to the movies. Always the movies. We saw truly everything—there was nothing we didn’t see!”
—Deborah

In the ’80s:

“I went on a lot of coffee dates. At the time, I was mostly going on dates with other students so we’d call them ‘study dates’ and we’d drink coffee and open our books. Within an hour or two, we’d be at a pub.”
—Kathryn

In the ’90s:

“When I was really dating, we were out every night. I’d go on a date—out for drinks somewhere—and if it went well, we’d end up on a dance floor. Actually, I used to frequent this place called Johnny’s in the West Village. It was ultra-divey which made it that much more fun when we’d end up at a club.”
—Ryan

In the 2000s:

“I was pretty hard and fast about sit-down dinners. If I was bothering to show up for a date at all I wanted it to be good and substantial, you know? Odds were, I wasn’t dating more than one or two people at the same time, so I wasn’t trying to squeeze a bunch of dates into my schedule. I had three restaurants I loved for dates—two in the East Village and one in Brooklyn Heights.

I’d say if the date itself was less than two hours, it went poorly. That would mean that we hadn’t connected—dinners can last five hours if you want them to.”
—Dave

In the 2010s:

“I always just do drinks. I think that’s probably the most normal. We meet up at a bar, have one drink and part ways if it’s bad, have 3+ drinks and hookup if it’s good, and…I’m still working on some kind of normal, sustainable in-between.”
—Emma

“I don’t date that much—so dates, when I choose to go on them, feel pretty special. Once I went to four spots in one night: a three-hour dinner at a restaurant, dessert somewhere else, drinks a third place, you get the idea. Another time, I had a 24-hour date that I made a vintage shopping itinerary for. I think that’s how you get to know people best.”
—Lily

Today:

“We’re all underage so sometimes we’ll meet up to go to a party but usually we go to public places like a Starbucks or a park. Sometimes people come meet us and we all just hang out with our friends because the date will be awkward if we do it alone.”
—Nicky

A Go-To Dating Anecdote…

In the ’50s & ’60s:

“I met Al in 1956 when we starred in an off-off-Broadway play. We lived together until we married the following year. Earlier, though, our first serious date had ended with sex and disaster. I don’t want to go into the details, but, of course, we patched things up. Then we went on to act opposite one another on many occasions in many different shows. And, well, he was my life partner.”
—Marydean

In the ’70s:

“If I hadn’t met my second husband while walking my dog, I think I would have given up dating altogether. It wasn’t enjoyable for me, exactly. But now, 27 years and one son later, I know that the intuition I’d had about giving this a chance was absolutely correct. Living in this city has provided a wealth of opportunity for me, dating and otherwise, but what I’ve learned, most of all, is that the key is knowing what does and does not feel right to you.”
—Deborah

In the ’80s:

“I do remember one date in particular where I went to a boy’s apartment that was a six-floor walkup. I thought I was going to pass out on the stairs. And once we were there, he made breakfast for dinner—pancakes and orange juice, with a record playing. It was such fun.”
—Kathryn

In the ’90s:

“My kids would kill me if I let you print any of my best dating anecdotes. That’s a conversation for another time…off the record.”
—Ryan

In the 2000s:

“Well…like I said about my spouse. We met playing on a soccer team together on the Lower East Side. I think that’s just the most wholesome story.”
—Dave

In the 2010s:

“I’m scared if I tell you, one of my former first dates will read this story…”
—Emma

“I went on a date with someone whose age I didn’t know—I don’t think he knew mine either. Eventually, we determined that I was five years younger than he thought I was, and that he had two children…while looking shockingly hot for a dad.”
—Lily

Today:

“Umm….well I dated a boy for a while who Catfished me. He said he went to a different school and had a different name and stuff and it was kind of a big deal. It was a whole thing. But yeah, stuff like that is pretty scary, especially while I’m still young.”
—Nicky

Graphics by Lorenza Centi.

Get more Brain Massage ?