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 2/2/2023, Updated on 2/3/2025
People like to ask why I’m doing this and, well, it’s mostly because: why not? I’m at a stage in life where I want to actively date and remain single as a solo poly bi woman, so why not learn something about myself in the process. I don’t see this as a way to make fun of anyone I go out with, no, on the contrary, this is a way to make fun of myself. Hell, if I went out with someone, I’m the one who picked ‘em.
That’s on me. Back in 2019, I went to intensive outpatient therapy. When I did my intake and answered all the questions about the abusive relationship that led me there, the lady said, “Oh, you’ve got a broken picker.” I also heard someone say that on Darcey and Stacey or maybe it was 90 Day: The Single Life, I don’t know. Either way, it resonated with me. We all have a picker, so what is mine tuned into? What is up with my picker? I didn’t date for a little over a year after that and, well, that pretty much brings us up to where this project started.
Some people ask: What are the worst dates you’ve been on? What did you learn? In order to fine tune my picker, I compiled a list and sincerely asked myself: How the hell did I get myself here?
Again, I’m reiterating that I am polyamorous and have been for a decade now! So, hey, I date a lot and for a lot of my early poly years, I gave a lot of people chances. I can genuinely say, I don’t have a type! If you lined up everyone I’ve dated, I don’t think there would be any similarities.
Also, somewhere around the age of 20, I decided life was mostly worth living for the story and became incredibly reckless with my one human body on this earth. OkCupid dates with people who didn’t even have face pics? Ok. Craigslist dates? Sure. It was 2010, things were different (no they weren’t, I was dumb).
I have a lot of bad dates to learn from.
The Pan
When I was 23, an opera singer asked me out. This was a normal thing in Chicago, where I guess there’s some sort of opera college, I don’t know. Either way, I thought that was an interesting career! I’ve never gone out with an opera singer, why not see what they could introduce me to!
And we did have a great date. So great, that afterwards I invited him back to my place. When we get there, things are pretty normal until he starts asking about my dating experience and kinks. Honestly, questions like this don’t really throw me off on first dates. We’re all trying to see if we vibe, right? Friends have told me, no, as soon as a guy says, “So, do you have any kinks” on a first date, that’s a red flag. Maybe they’re right!
Because this guy goes: “Well, I have a kink, I like to heat up a frying pan and cum in it.” Then he asked if he could tonight. I said no, because, well, I eat out of those and absolutely not and also that sounds dangerous! And ew! And why? I guess I kinkshamed because he left not too soon after.
But not before he revealed that he lived in a studio apartment with his mom.
I’m sorry, how do you have a kink that requires a kitchen when you don’t have a wall between you and the only place where your mother rests?
The Rope
I’ve told this one before on podcasts and Twitter and Tiktok and I used to do it as a story at The Moth and some other live events. People say it requires a trigger warning so THIS IS THAT. Keep scrolling if you don’t want to read something kind of scary.
This was my very first Tinder date! I think I was 23, living in Chicago, doing my single life thing. I lived with two boys who were college freshmen, we drank 40s and cried to Elliott Smith songs. I was fresh out of a 4 year relationship and had bounced between OkCupid dates for a bit. Eventually, someone told me to try Tinder.
Back then, you could connect it to your Facebook profile and it would show you any mutual friends you had. That’s weird now, but it made sense then! I matched with a guy who knew a bunch of people from my college and we started chatting. We go out to get drinks, everything during this part of the date is incredibly boring and normal.
After, I invite him back to my place because, well, he was hot and that was mostly where my interests were at the time (an issue with MY picker). We watch SNL, we start making out, suddenly, he stops. He puts his hand on my cheek, caresses it and asks, “If I brought all my friends over here, would you suck all of their dicks?”
This is obviously a ridiculous and horrible question. I started making jokes! How would that even work? Would you all take a number? Put me on a lazy susan and spin me around? That made him mad. He slapped me. I kicked him out, threatened to have my roommates beat his ass (god bless them, they were 19yo vegans with a pound of body fat between them). After he left, I went back upstairs and noticed he left a bag. I immediately start going through it so I can keep whatever money he has in there.
The only things inside were a diet dr. pepper and a six foot rope.
I kept both of them for awhile because no one ever believed me when I told this story. Anyway, I’m alive.
Back-Up Date
This one…to this day, even I don’t know how I ended up in this situation. An OkCupid date asked me to go to an arcade bar in good ol’ Logan Square, Chicago. I show up and there are two girls with him. He comes to greet me and takes me to the bar, buys me a drink and says they’re his friends from Northwestern. They also wanted to check out this bar so they followed us out, but won’t be bothering us. Whatever! I called this one a wash as soon as he said “Northwestern” and “I live in Evanston.”
As the night goes on, these girls are in fact bothering us. They’re sitting with us the whole night and only talking to him. I’m trying to ask questions and get in the convo, but it is very clear they are interested in this guy. Eventually, he leaves and Girl 1 admits she’s in love with the guy and has liked him for a long time. She then reveals that Girl 2 is actually a sex worker friend she hired because she thought offering the guy a threesome would make him like her. So that was her plan for the night!
I don’t think the guy was aware of the plan, or at least I thought he wasn’t, because when last call came, he was saying bye to them and asking to go to my place. Should I have stood in solidarity with the girl I just met who liked the guy who asked me out and wanted to bamboozle him with a threesome? Maybe! I didn’t, though! Instead, I brought him back to my place (he was hot!). This ended up being a mistake though because after hooking up, he tried to fall asleep. You know, that heavy fake sleep where you can tell a guy doesn’t have money for an Uber home so he tries to just sleep over?
Yeah, I don’t let that happen. In fact, I never let people sleep over. I woke his ass up, YOU GOTTA GO! He’s all, “I live in Evanston, it’ll cost too much blah blah, it’s so far!” Truly not my problem! So, what does this guy do? He CALLS GIRL 1 and asks if she can come pick him up! And, dear reader, SHE CAME TO PICK HIM UP! He then explains to me that he knows she likes him and keeps her around as a “back-up date” in case the girl he meets on an app isn’t hot. I didn’t tell him about the threesome thing, but he figured that’s what she was doing.
She got there at 4am and drove him home with all my pity.
The Berlin Wall
This one is pretty simple. I was in Portland on a work trip and when I work travel, I love to work fuck! I hit the apps and matched with someone who seemed pretty cool. We decide to meet up at a BBQ place and things are going great. We’re laughing, having a good time. We have similar interests! He invites me back to his place and I’m like, okay you have a place!!
The place is like, a big dilapidated Victorian home he shares with three women he reveals are part of his coven. Ok. There’s tons of creepy shit all over the house. Ok, whatever. I like Hot Topic. I listen to KoRn. We go up to his room, the paint is peeling from the ceiling. The mattress is clearly older than I am and everything is dirty and dusty. It’s a no for me!
I sit on the edge of a chair and start talking A LOT to make it clear I’m not interested in any sort of bed happenings. Somehow, we get on the topic of German history. I mention my history degree is focused on German history, I studied German and lived there for awhile! In reply to this he says, “You know I always thought Hitler had some good ideas, like what he did did make Germany stronger.”
Now first of all, let me say: this was a BLACK PERSON. OK! I could NOT have seen this coming! This was 2017, before Kanye! I, of course, start arguing with him. I point out that’s not true. That the Berlin Wall had a horrible impact on the country’s economy. That parts of Germany have never financially recovered. That it was actually an influx of immigrants and diversity that saved post-war Germany and absolutely NOTHING that Hitler did!
He disagrees and tries to argue back: He says the Berlin Wall fell “back in the 60s” so it wasn’t a big deal. I point out that the Berlin Wall fell in 1989, like Michael Jackson moonwalked across that shit. He starts making up other historical facts and just gets angrier and angrier when I correct him. What can I say, I was young. I had time to waste and I liked being right.
Eventually, he got so mad he just started yelling that I was a smartass and no man would ever love me because I was a cold, dumb woman who couldn’t take a man’s advice. I left.
Those are all my worst dates. Sure, I’ve also had just…y’know, bad sex, boring dates or dates where we don’t click, but these are the dates that stuck with me. I learned from these dates and I can say, since starting this project, I haven’t had any more experiences like these. Maybe my picker is fixed.