Joanna and I have both dated people in New York — but 15 years apart. I’m dating in 2020 with apps like Tinder and Bumble, but she dated in 2005 without apps, back when George W. Bush was president and Instagram wasn’t a thing. It made me wonder how different our experiences have been. So, we took each other on a date to talk about it…
ON MEETING PEOPLE:
Joanna: I met people out and about.
“When I was single, it was hard to meet people to go on dates with — I was always lamenting to my mom about it — so you had to stay open. I’d ask friends to set me up with guys, or I’d meet people at parties. Once I met a guy because he was rollerblading in Manhattan and he bumped into me and I laughed and he circled back and asked me out! I also met a serious boyfriend in a Kaplan LSAT class that I taught. He was a student and would draw pictures of me in his notebook during class, which was so cute.”
Kim: I meet people on apps.
“I would love to hit it off with someone at a party or be introduced by my best friend, for the ‘how we met’ story, alone! People on apps are a pretty mixed bag, and it can seem like a chore sometimes. But living in a big city yields an interesting array of people — I’ve met the most fascinating people online. I once met a guy who had run the New York City Marathon that morning, and we went out for drinks that night. We both happened to love education and ended up talking about Sesame Street for half the date! Some of my fondest dates were with people visiting for the week from another country — I’m still friends with a few.”
ON HOW OFTEN DATES HAPPEN:
Joanna: I went on six dates a year.
“I’d probably go on about six to eight first dates per year. If the date wasn’t great, but wasn’t terrible, I’d often give it another shot. There was no reason not to give people a second chance, because there was no one waiting in the wings — dating overall felt slow paced.”
Kim: I go on a date every week.
“For a while, I went on a date once a week or more. It’s so easy to set them up online. My colleagues laugh when I talk about ‘scrounging up a date’ for the weekend.”
ON SETTING UP THE DATE:
Joanna: The guy would call.
“In my experience, the guy would call and leave a cute awkward voicemail. Then I would call back and we would plan the date. It felt old-fashioned, in a good way.”
Kim: I do the asking online.
“On apps, the conversation can go on and on without any sign of an end, so a lot of times I’ll say something like, ‘Hey! We should go get drinks, yeah?’ They’re always pleasantly surprised, and it gets the ball rolling. When the convo switches from the app messaging system to texting each other’s phone numbers, it feels more personal. Like, ‘Ok, we’re doing this!’ Usually the day of the date, we’ll text each other inside jokes from earlier in our conversations. It helps a lot, because once you walk through the door, the ice is already broken. You’ve already been talking with this person, and you have a rapport.”
ON SNOOPING ONLINE:
Joanna: You couldn’t find much.
“I’d sometimes Google people but you didn’t get much info because people didn’t have as much of an online presence. Instagram wasn’t even around yet.”
Kim: I can find anything.
“I don’t know whether I’m ashamed or impressed with how well I can snoop on someone — give me two minutes and I’ll find their Instagram, Facebook and LinkedIn. You don’t even need to know their last name.”
ON DINNER VS. DRINKS:
Joanna: We’d go to dinner.
“I liked dinner dates because there was an obvious beginning, middle, and end, whereas drinks felt more awkward, like, ‘When is the date over?’ Dinner was more of a splurge, but since I didn’t go on that many dates, it was okay.”
Kim: We meet for drinks.
“Ten times out of ten, it’s drinks. It’s fun to meet for drinks, and if the date is good, you can continue the conversation (not a euphemism) at a second location where food is possibly involved.”
ON AN AGE RANGE:
Joanna: I stuck to my own age.
“Guys would usually be around my age since I met them through friends, but then I met Alex, who is 13 years older than I am. He would’ve been outside my specified age range if I had been online dating!”
Kim: I loosened things up.
“I used to set my app parameters for guys within a three-year age range (younger and older). Then my friend Leslie urged me to up my parameters… like WAY up. I was skeptical — I thought I wouldn’t have anything in common with someone older, but it was actual a total game changer. My current boyfriend is six years older than I am, and it’s the perfect fit because we’re still in the same decade, but our views on pop culture and music are completely different! It’s fun to learn those things from each other; plus, his self-awareness and life perspective are an added bonus.”
ON SEXUAL TIMING:
Joanna: It’s all about what feels right.
“I would kiss on the first date if we hit it off, and then I took a really long time to sleep with people. Not for any reason except that’s what felt right to me.”
Kim: It’s all about what feels right.
“I pretty much always kiss on the first date, unless it’s a dud. Same with sleeping with someone! Since I’ve had lots of previous conversations with them, I already have a sense of who that person is, I feel closer to them, and it becomes easier to kiss or sleep with them, sooner. I used to follow the don’t-sleep-with-someone-on-the-first-date rule, and after a while I just didn’t see the need to follow it anymore. It’s all about what feels right, in the moment.”
How has dating changed for you over the years? We’d love to hear what you think…