10 Years of Digital Dating, 52 First Dates or: How My Exes Found Love
From the Archives: 52 First Dates
In 2023, Ashley went on a new first date every week of the year until she fell in love. Pieces from this experiment will be up weekly on Deep Trouble for paid subscribers.
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Originally published 1/4/2023, Updated on 12/16/2024
I am not a dating expert. Not at all! This is a warning I 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 also solo poly which basically means I’m always single. I date people. I have relationships, but I’m not interested in a primary relationship1. 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. This is about what that looks like.
Over a decade of ENM dating, I’ve figured out 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.
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 what I thought when I graduated from college in 2013 and up until I moved to Los Angeles in 2019. I loved dating apps. I loved going out for drinks or coffee or DIY shows. I went from a small town to Chicago and 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’ll shutdown my roster, but mostly I really enjoyed sitting across from a stranger; getting a peek into someone’s life.
When the pandemic hit, I lost that part of my social life. I tried Zoom dating, but it mostly felt weird2. I met people who were nice and great, but it’s hard to find a connection with someone when your roommate is 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? So, I did. Until the summer of 2021.
The vaccine came out. The streets were hot. I decided to try dating again, but I had no idea what I was doing anymore. The feeling of just being around someone again overtook the “do I actually even like this person?” part of my brain. I was learning how to connect and flirt all over again.
I’d been in a long relationship with solitude and I wasn’t sure how to dive back into a social life3. 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 needed 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 before they were full of bots. 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, as the puriteens say.
I don’t actually think that’s true, but it was suddenly easier than ever to meet someone who was into whatever weird sex stuff you were into. It made hooking up easy. But then there was a mini revolt against apps like Tinder and Grindr when Bumble and Hinge made people realize they could 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, but 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 look at 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 in 2023. 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! 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.
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