In 2023, Ashley went on a new first date every week of the year until she fell in love. In 2025, she’s revisiting these weekly pieces on Deep Trouble to see how well this experiment really worked.

Originally published 2/9/2023, Updated on 2/10/2025

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We have another Feeld date ,everyone! This is my 2nd Feeld date since starting this. This one was more the usual Feeld speed. Honestly, getting coffee with the first Feeld date might’ve been the first time I’ve ever done that with that app. Usually, Feeld dates want to meet up late at night.

Also, who can remember? I’ve been on Feeld since it was 3ndr. I have made some of my best friends and greatest enemies thanks to that app. For someone like me (polyamorous, bisexual, etc.1), Feeld dates are usually great! It’s the app I used to recommend most to people who want to try non-monogamy or something else less mainstream.

If you’re unfamiliar, Feeld started as an app for unicorn-hunting couples (3ndr). Then it evolved (and got sued into changing its name) into an an app for queers, open marriages, non-monogamous demisexuals, fetishists and just straight up kinky people who know how to communicate. And also a lot who do NOT know how to communicate (it’s still a dating app). At its core, though, it’s an app for people who do not need me to define what any of the above terms mean. Tinder, Bumble, Hinge…it requires so much Polyamory 101 moments. It can be tiring.

In 2024, Feeld rebranded again into the inclusive dating app for cool sexy city people. They make a magazine called AFM (A Fucking Magazine), with advice and essays. They throw Manhattan parties with Woody Allen in attendance. The user interface has been updated, causing constant bugs and issues. It’s not the app I recommend as much anymore because it’s been overrun with straight couples unicorn hunting and fuckboys. Of course, I could be biased.

Before this pivot, Feeld did local queer events in different cities (including comedy shows hosted by yours truly). It created a user base that felt organic and true to the local poly/kink scene. You’d see people at shows, then you’d see them on the app. Now, it feels like the app wants to attract people who are impressed by the big names they publish or invite to literary salons. There are fewer people from the actual scene and more people seeking experiences they’ve only read about.

It also isn’t as hard out here for us non-monogamous people or kinksters these days. My friends say Hinge and all the popular dating apps have added non-monogamy and kink options. You don’t have to feel like a little freak forced to use one app anymore.

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In 2023, Ashley went on a new first date every week of the year until she fell in love. In 2025, she’s revisiting these weekly pieces on Deep Trouble to see how well this experiment really worked.

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In 2023, Ashley went on a new first date every week of the year until she fell in love. In 2025, she’s revisiting these weekly pieces on Deep Trouble to see how well this experiment really worked.

Originally published 1/30/2023, Updated on 1/27/2025

I’m also donating my Substack from this month to wildfire mutual aid, so if you subscribe right now, it’s for a good cause.

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Hey! Thought I finally gave up on this? Thought a man I rejected murdered me1? No! I just stacked up some dates and then went into hibernation mode because I got my period. But Ashley, you’re a modern woman, a feminist, what’s wrong with dating on your period or period sex? Well, nothing! It’s just that I personally have endometriosis, so physical movement hurts during that time of the month. I need to stay home with a heating pad because my body is actively fighting against me.

I knew I’d be out of commission, so I used the previous week to pile up on coffee dates and drinks. That’s my preferred style of date. Meet someone, enjoy a drink, get on with your day. If things click? Keep hanging out! Make more plans! Everyone takes dating (and everything) too seriously now. Popping in from 2025 to mention the latest wild thing I’ve seen online: everyone is mad about this guy who posted a pic of his friend who was excited his girlfriend got an IUD. A thing that has nothing to do with anyone else is making people mad because it “centers” a man’s pleasure.

People get IUDs for so many reasons. In fact, I switched from copper to hormonal a few months ago. It helped with the endometriosis I mentioned above. But also, women enjoy sex too. It seems very likely this was a choice she made for her own reasons. There was also a thread where people were shocked by the number of men the women in Sex and the City slept with. They were like, the women in this show about sex are having too much sex. Someone broke it down and pointed out Miranda is a women in her 30s and that averages to about 3 men a year.

I know the conservatives have one, but it’s wild that even something like birth control is questioned as anti-feminist now. I do not get what is going on. Oh well.

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In 2023, Ashley went on a new first date every week of the year until she fell in love. In 2025, she’s revisiting these weekly pieces on Deep Trouble to see how well this experiment really worked.

Subscribed to 52 First Dates last year? You get Deep Trouble free for 3 months! Check your inbox for details, you should already be subscribed.

Originally published 1/17/2023, Updated on 1/20/2025

Also, consider donating to these GoFundMes to help people who’ve lost their homes! I’m also donating my Substack from this month to wildfire mutual aid, so if you subscribe right now, it’s for a good cause.

I know I said only a week ago that flirting was fun again, but I burned through that like a copy of Spare1. Once you get back into the rhythm of checking dating apps, replying to texts and actually going out to meet people, the thrill goes away quickly. In fact, friends quickly pointed out that one date a week was actually pretty low for me. Hell, in my twenties, I used to stack multiple dates into a day2. I saw a woman do this on Tiktok and people were VERY angry with her as though this were a new thing she invented, but people across the gender spectrum have been doing this for centuries.

Checking in from 2025 here to say that a clear example of this is pretty much how mad Twitter gets any time I mention polyamory. They simply cannot think of a reality where a woman knows she is polyamorous, is happy with that choice and is so firm in it, she can joke about it. It’s a reminder of just…how online the whole being online thing is. I can’t say in my actual every day life any online conversation around my relationships has been accurate.

Recently, I haven’t wanted to go on 52 first dates, but I have wanted to socialize again. It’s been years since I’ve cared enough about going out to have a regular dive bar. I hangout with my friends and the people I like, but I used to be outside. Just truly, outside. If I can read 100 dumb opinions a day on Twitter, why not go outside and meet people who probably won’t have very online opinions? I still live in Los Angeles, but it’s gotta be better than reading tweets from people who weren’t alive during the Bush administration.3

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In 2023, Ashley went on a new first date every week of the year until she fell in love. In 2025, she’s revisiting these weekly pieces on Deep Trouble to see how well this experiment really worked.

Subscribed to 52 First Dates last year? You get Deep Trouble free for 3 months! Check your inbox for details, you should already be subscribed.

Originally published 1/9/2023, Updated on 1/13/2025

Wildfires have recently destroyed parts of my current home, Los Angeles. It feels like perfect timing that my post about falling in love with Los Angeles before I could actually find love here is being reposted.

I love LA and ask you to consider donating to these GoFundMes to help people who’ve lost their homes!

I’m only 9 days into this little “experiment,” but I have reached my first noticeable milestone: flirting is fun again. I’ve always liked flirting. I used to be really good at flirting, back in the day. Back before I stopped leaving my house. When I still enjoyed people being closer than 6ft to me. When I started dating again post-vaccine, I knew I was rusty that summer of 2021. I just said and did so many embarrassing things. One time a girl kissed me and I said, “Good stuff. Gang. Gang.”

I felt so out of practice with flirting and casual conversation, I dated someone for months just because I liked that I felt invisible around them. I could say nothing and they didn’t care. Sometimes, I felt like I could just disappear in that moment and they probably wouldn’t notice. Hell, I don’t even think they knew my actual name.

I remember asking them how they felt about polyamory and monogamy. They asked me why? I said because I’m polyamorous (a fact that is clear on all of my dating profiles, social media, and if you listen to me talk about my past for at least 10 minutes1), so maybe we should be on the same page? They were shocked: almost six months into our relationship, they had not noticed this about me or remembered I ever said it.

I wasn’t even mad. I was just happy I could exist around someone who did not care to listen to me, Google me, read my tweets or show any interest in me. It was a no pressure situation. We smoked pot, watched TV and I played with his dog. We didn’t go out. There was no pressure to escalate the relationship or meet each other’s friends.

Sometimes you need that. Post-COVID solitude, this was a great way to ease back into being around new people. Obviously, now, I’m in a healthier place and I enjoy the company of people who, y’know, actually notice me and even like me, but at the time, that was what I needed.

Now that I’m actually forcing myself to date with intention, though? Oh god, flirting is necessary. Flirting over dating apps. Flirting over text. Flirting over a drink. It turns out I’m not the only person who got bad at flirting, though! I am running into so many people on the apps who simply do not know what they are doing!

Often, men think flirting is just bragging about themselves or saying something way too sexual. Taking the time to actually find people I have e-flirt energy with has been helpful. And, it’s how I found my second date.

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In 2023, Ashley went on a new first date every week of the year until she fell in love. In 2025, she’s revisiting these weekly pieces on Deep Trouble to see how well this experiment really worked.

Subscribed to 52 First Dates last year? You get Deep Trouble free for 3 months! Check your inbox for details, you should already be subscribed.

Subscribe now

Originally published 1/7/2023, Updated on 1/6/2025

I’m doing this project because I’ve had the hardest time forcing myself to get out into the world since the pandemic. I’m happy! Life is great! I saw that tiktok where the guy is like “I think I healed too much cuz…I don’t like anyone,” laughed and went “same.” But, true healing is when you look at the world and the people in it with openness and optimism, right? I guess. I am trying. Just like, not too hard.

For my first date, I played it very casual. I tried scheduling and arranging a date for the week, but that was pretty difficult. Usually, I use dating apps the way most people do: chat a bit and let’s hook up TONIGHT. I’m not looking for midnight apartment visits, though. I want real dates! Like the great Meredith Grey said: I want heat, romance. Let’s grab a coffee or a drink. Let’s see a movie or go dance. These are things that require planning.

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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.

Subscribed to 52 First Dates last year? You get Deep Trouble free for 3 months! Check your inbox for details, you should already be subscribed.

Subscribe now

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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