10 Years of Digital Dating, 52 First Dates or: How My Exes Found Love
Welcome. I'm going on a new date every week of 2023. Why?
I am not a dating expert. Not at all! This is a warning I always make clear because, well, I don’t want to be a dating or relationship expert. I’m a comedian and writer who has talked about my experience with polyamory and dating a few places. It isn’t my goal to be your go-to source for How to Polyamory. I’m just a person who likes to meet people. I’m solo poly which basically means I’m always single. I date people. I have relationships, but I’m not interested in a primary relationship. Instead, I let relationships exist on their own terms. It requires a whole lot of direct communication to figure out what you want from each other and what that looks like.
Over the last decade of ENM dating, I’ve figured out a few things I like and don’t like. I’ve learned some things and seen some hilarious things. The question I get most is: if you’re already seeing people you like, why do you need to see more? That’s never really made sense to me, though. I have friends I really like, but I still look for new friends. For me, it’s about the joy of meeting and experiencing new people. Creating new dynamics and discovering new ways to connect with people. It’s one of the special things we get to do on this planet as humans, so why not jump in and get to know people?
At least that’s how I was when I graduated from college in 2013 and up until I moved to Los Angeles in 2019. I loved trying dating apps. I loved going out for drinks or coffee or DIY shows. I went from a small town to the city of Chicago and truly wanted to date my way through the city. I made friends. I made enemies. I had great relationships, short ones and horribles ones. I liked dating so much, I even did a project where I dated every astrological sign a month at a time for a year just to see if there were any differences. I do have periods of monogamy or I shutdown my roster, but mostly I really enjoyed sitting across from a stranger; asking the usual “So, what do you do?”-type questions and getting a peek into someone’s life.
When the pandemic hit, I lost a huge part of my social life. I tried Zoom dating, but it mostly felt weird. I met people who were nice and great, but it’s hard to find a connection with someone when you can hear their roommate coughing through the walls. Also, as much as I like dating, I also love spending time alone. I was absolutely happy to sit back in my bedroom without FOMO hanging over me. I’d been a non-stop dating train for 7ish years, why not take a break? That’s what I did from the beginning of the pandemic until the summer of 2021.
The vaccine was out. The streets were hot. I decided to try dating again and I had no idea what I was doing. The fun of just being out in the streets again overtook the “do I actually even like this person?” part of my brain. It was like learning how to communicate and flirt all over again. Or that feeling when you get out of a long relationship and you aren’t sure how to dive back into single life. It was mostly bad. So many bad dates and situationships that pre-pandemic me would’ve known to steer clear of. I lost my dating-senses and I wanted to get them back.
When I left my ex-fiancé in 2013, I moved to Chicago and was lucky enough to have nearly every dating app at my disposal. I tried them all. OkCupid, early Tinder, Plenty of Fish, all of it. It was the pinnacle of what is now described as “hookup culture” or the thing that my generation used to destroy sweet sweet monogamy and marriage. I don’t actually think that’s true, but it was suddenly easier than ever to meet someone who was into whatever weird stuff you were into. There was then a sort of revolt against apps like Tinder and Grindr when things like Bumble and Hinge made people realize they could actually find their spouses on these things.
Above is a little timeline of the apps I used and what I thought of them. Maybe the love of your life is out there, they’re just on some weird app you’ve never heard of. It’s also interesting to look at how digital dating has morphed over the years. We used to give people within a few feet our location and go, “Hey, if you happen to be around, wanna go on a date?” We would answer hundreds of questions on OkCupid in the hopes of finding a 99% match. It was a wild time. Now, it’s not nearly as exciting. Comedian Kath Barbadoro summed it up perfectly:
Anyway, I am trying to date again and everything about it is harder and not nearly as fun. Not only because apps have changed, but also because, oh man…did I mention how much I love being alone? Solitude is so wonderful and it is like pulling teeth convincing me to leave my apartment. As a resolution this year, I decided to force myself out of this rut with a project called 52 First Dates - every week, you go on one new date. Easy. If I make myself go on a new date every week, it should help me get back into the swing of things, right? Maybe. Let’s find out! I did some googling and someone did this on their blog awhile ago, so I’m definitely not the first person to think of this. Did it work for them? I don’t know, I didn’t read it all! Also, as someone who doesn’t practice monogamy, why not try it? I have nothing to lose.
This will be my weekly update. Mostly, if I have this, I’ll be forced to hold myself accountable and actually go on dates! Why am I doing this? To make my way back to myself! To reignite my optimism in humanity! I want to believe that people are mostly great and worth meeting again.
Last year, I was also working on a piece for a publication on the decade anniversary of Tinder and what it was like dating digitally. For the piece, I was interviewing exes and partners I met through dating apps to get their perspective on how we met and how the dating app we met on shaped their experience (if it did at all). As a bi-poly person who loves to date, I had a large variety of people to hit up. I reached out to about 10 people across the gender and race spectrum. Some who were still poly and some who had gone back to monogamy. A few of them had even found love and offered their advice. Overall, six exes were down to chat. three justifiably ignored me and one said it was a desperate ploy to get back together (it was not).
The publication, however, was pushing me to do a photoshoot with my exes, which felt weird. First of all, they live all over the country, so the logistics didn’t make sense. Second, we promised everyone anonymity since all of my partners weren’t out or comfortable sharing their identities. It felt like that just wanted to gawk at some weird polyamorous people. The editor kept pushing me on pictures even though I refused multiple times. The vibes felt bad. I decided to put the story back on my shelf.
As 2022 came to an end, I started listening to the transcripts again and what they were saying lined up with this project: If you wanna find somebody, you gotta get out there and give people a chance. I’ve become so used to being alone during quarantine, I lost interest in new friendships and relationships. I felt like a completely different person who had to find themself again. The things they said made me hopeful and encouraged me to get out there again. Maybe they’ll motivate you too.
After reaching out to people who dated me (a benefit of queer, ENM dating is that you usually just end up friends), what did my exes who found love have to say about it? Names have been changed.
Ben
Relationship dynamic: Long-distance FWB in open marriage
How’d you find love?
I tried OKCupid, eHarmony, but there were only a few thousand people on OKCupid back in 2004. The etiquette of online dating hadn’t been established yet. I actually met my wife in real life at Trader Joe’s. (At this point, his wife joins the call because she remembers the story better)
Tania: I was at Trader Joe’s. I’d been dating. I was divorced and I’d been on the apps for a couple of years. I felt like I wasn’t meeting anybody worth my time. Anyway, we saw each other in the frozen food section. I happened to go on the same subway and I kind of just walked past him and gave him a little smile. And he asked if I was from California. (The rest of this is adorable banter between the two of them that has been cut so we don’t all vomit, but it’s cute and gives me faith in love again).
How do you date now?
Ben: I can really only date on apps now. It’s hard to meet people in real life as a person who’s married with a wedding ring. Explaining my situation? I wouldn’t believe it. My wife and I started non-monogamous, we were both just very conscious of the fact that we wanted stability, but we did not want monogamy. We like being with the same person and building a family. Within like three months of dating, we’d seen a couples therapist who specializes in non-monogamy. We each had a session. We had a session together. We really got a sense of what our expectations were. But it’s been great because on dating apps, all of that is written out. My pic, pictures of her, a link to their profile.
Tania: We’re married, we have kids. We’re happy. Everything’s good. And we’re still non-monogamous. But dating apps let us meet people who get what we’re doing.
Advice?
Ben: I think the advice is like, cool and breezy. Thats what I tell everybody. Thats what someone told me once, when I was asking dating advice as I got older. Keep it cool and breezy.Jake
Relationship dynamic: Previous open marriage, now monogamous
How’d you find love?
I met my wife on OkCupid. I met people on J-Date. But we all saw OkCupid as the cool app at the time.
How do you date now?
We’re monogamous now, but when we were open, OkCupid made it easy to put it all out there, but it was odd switching to Tinder. OkCupid was very extensive-multiple paragraphs, questions, percentages. Suddenly it was just a picture and a few sentences.Advice?
I wasn’t looking for marriage when I met my wife. For some people, I think having a real sense of purpose can be a good thing. But I think that, you know, success is about openness and going with the flow with a sense of yourself.Sandy
Relationship dynamic: Situationship to good friends
How’d you find love? (Sandy is currently single, so we talk about us)
When we met, I saw you were poly and I thought that was appropriate for me at the time. I felt like I was poly at the time. I liked that you were into history. We used to watch The L Word together. I think I knew it wasn’t going to work because of the way you texted. Instead of sending everything at once, you’d send like 3 individual texts and I was like, “Oh, we’re going to be friends.” (It is true, I do text this way).
How do you date now?
I’m less interested in more traditional ways of meeting people. I’m not interested in going to bars and shows as often. So I’m even more reliant on dating apps to meet new people. I’m just sort of ambivalent towards online dates. I think part of it is the pandemic, I don’t want to just meet random strangers for casual sex or a one-off date. I kind of just want more permanent people.
Advice?
I used to tell an old friend: mention your favorite Pokemon, but these days, I say just volunteer trivial information about what you’re into. Talk about the shows you’re into and you can find somebody who has a mutual interest with you. I think thats what makes OkCupid better? Everyone used to use it like a Livejournal. They would record every movie or band they’d ever seen. You don’t need to do that, just do three. Three is good.Lee
Relationship dynamic: Dated her and her primary partner
How’d you find love?
My sexuality is pretty fluid. I’m on the asexual spectrum. I guess demi is the best label for me. I’ve been married to a woman for two and a half years. We didn’t meet on a dating app, but we have a funny dating app story: I moved to a new city with a partner and we broke up. I started taking dance classes to find community and I reached out to the teacher like, “Hey, hope this isn’t weird, I’ve been in your class a couple weeks, but do you know anyone looking for a roommate? I suddenly need a place to live.” She was like, no worries, I have an extra room you can crash in until you figure it out. That was six years ago, I never left. Then she got out of a relationship and we were gonna help each other stay single. So, we both got back on OkCupid and we were setting up our profiles and looking at each other’s matches and we realized we were each other’s highest at 98%. (Aw.)How do you date now?
My wife is not monogamous and I’m fairly monogamous. I’ve had the most fun with FetLife. I’m looking toward exploring kink without sex with other people, so FetLife makes that easy. Yes, there are people looking to do nasty stuff, but there’s a directness about it that I like. I feel like thats lost on a lot of other apps. The beauty of dating apps is being able to put out there exactly what you want.
Advice?
I feel like, as a cultural narrative, we have this notion that like, if a relationship sucks, we should do everything in our power to work it out and make it work. And my advice would be: if the relationship sucks, you can leave. Like, theres still are so many other people. So yeah, date a lot. Get exposed to a lot of different types of people. That’s the most fun thing about dating, but also, like, if it doesn’t work, let it go. Especially if you’re in a big city. Some people will separate sex and romance. Some people can’t. Some people are looking for both. I don’t know if hookup culture is the culture of casual sex without commitment or a long-term goal. I’m very confused by the moral panic around hookup culture.
With all this advice in mind, I made some rules and set out to start going on 52 first dates:
One first date a week, but I can still keep seeing people I’m already seeing.
Tell people what I’m doing because why waste anyone’s time? I won’t be sharing any personal or identifying information, but I always like to give people the opportunity to opt out on the experience that is me.
Dates can come from anywhere: dating apps, IRL, social media. Whatever.
So, will this work out? I don’t know! I’m just excited to step back into life in a way I enjoy. I’ll be sharing insights from each date here every week. For free, you’ll get 2 emails in your inbox a month with some thoughts and quips on dating and romance from someone you think is funny.
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