This is a ranking, from worst to best, of everyone I casually dated after the end of my Long Relationship in June of 2022.

In last place (12 & 13:)

Left hand path guy 1 & 2: I went on two dates with two different men in a short period of time both at Left Hand Path. I don't remember their names and something about the way they looked kind of similar and had unremarkable personalities made me feel bleak. I remember one guy had a tattoo of a jack o'lantern because he "liked Halloween." I stopped dating for several months as a result of this.

11: P: He owned a yogurt shop in New Jersey that he drove me to in his car, this was probably the highlight of our relationship. Actually the highlight of our relationship was probably when he put Espresso on in the yogurt shop for me. He was kind of snippy with me once because he thought I was romanticizing having dated a bartender. He was like, if he's a bartender in order to be an artist he should be famous if his art is any good. I was like, it famously doesn't work that way. I broke up with him in person which was good practice. 

10: D: Frequently mentioned two things ..... that he had gone on a US tour with some band, and that his mom was the mayor of a prominent New York suburb. Okay.... #WHATELSEYOUGOT. On our first date we were sitting on a park bench and his friends came up to us and invited us to a very fancy rooftop bar with them. We went (was this staged???) and I was really underdressed, people were in cocktail dresses taking pictures of the skyline and I was wearing one of Alex's chore coats that looks like it has a cum stain on it. He does keep a blog I read sometimes

9: M: This was my first ever date meeting up with a random guy from the internet. I was soooo nervous but we had a nice time. We had a lot of book overlap, I was like damn you know who Lauren Berlant is? His mom was very low-grade famous and he had no job. After we broke up he went to a coding boot camp and Alex went to some talk he hosted???????

8:M2: Five minutes into our first date he asked me if I wanted children. I was like is this normal?? He was the second guy I ever internet dated. He was mild and sort of boring but ultimately sweet and he had a nice, very comfortable apartment. Although he only had one tiny bookshelf and it was mostly full of yearbooks ...... He described his family's wealth as "gatsby-esque," like he was one of the original rich people settling on Long Island or something. At first this was fun for me, he let me try an extremely expensive tequila and it tasted soooo sweet. But then he started to annoy me, I was like you have every imaginable privilege, why did you major in marketing??? And he wouldn't show me his penis. The whole time we were dating we were both seeing one other person and eventually I broke up with him. Then he was like, we should still be friends! And so we saw a movie and he was like Caitlin is my girlfriend now and I'm going to sleep over at her house after we watch this movie. I was like okay we don't need to hangout

7:M3: I can't believe I almost forgot this guy when we dated for like half of last summer. Honestly quite similar to M2 in that he was mild and polite and had a nice apartment. Both of these M's also had a sort of boring music project. Which I wish them both the best of luck on 

6:L: L & I met because I was ordering a coffee and she said, "you with the green pants." We went on one date, I tried to break up with her, and then we ended up in this protracted lesbian thing that concluded with her coming to see me run the marathon even though I told her not to. The issue is that she's smart and a lawyer and has the gift of the gab which is compelling to me. Sometimes we try to be friends 

5:R: This one was fun, I liked our dates (a lot of ice cream) and this guy was funny and had good social skills. Unfortunately he was a serial cheater. I put on the Cocteau Twins at his apartment and he was like isn't that a little obvious or something.............. sorry I don't want to listen to The Grateful Dead

4:Z: I don't really know why but I loved this guy. He was a drummer in a russian folk band and a software engineer but he was sort of secretive about the software engineer part. We only went on three dates, maybe he didn’t like me that much or maybe it was the off color thing I said the first time we were trying to have sex. We walked around Bushwick on our first date and we went through an alley lined with huge containers filled with bones. We had possibly my best second date after, maybe because I showed up in a really good mood because I had just won an Instagram giveaway. I was like look out, I'm in a really good mood, I just won an Instagram giveaway. We just sat in the park drinking spindrift because I was sober at this time. When we were kissing goodbye near some citibikes, an old man yelled "GET A ROOM!!!" at us, which tickled me.  Anyway he broke up with me 

3:D: D was nonbinary but felt our relationship was very lesbian. We had a nice first date, it was the first time I had slept with someone on the first date and I was proud for being totally sober. Our relationship was fun but moved too quickly for me. They are earning a high ranking on this list due to a) taught me some good stuff about tarot b) I wanted to hit it after we broke up which they traveled a long way to do and were extremely cool about c) they fixed my broken laptop screen d) I like them as a person even though we were not meant to be #partners. thank you D

2:V: Honestly he deserves probably a lower ranking, but the build up to our relationship was very fun, we spent several months in the will they won't they space. We had our first kiss under a yellow tree. Shortly after that we got ice cream and my ice cream fell out of the cone onto the ground and made a funny splat noise. Then we went to his room and I picked up an egg and it turned out to be an instrumental, shaky egg, which I loved, and then I started to notice a shaky egg sound in so many of the songs I listened to. Okay but he loses about a million points for only having sex with me during the work day ????????? (?????????????). Like we would only fuck if we were both not busy for 1.5 hours at our remote jobs. What kind of sick

1:R: Awww, R is a sort of rare beloved figure in the Ashley dating history. We dated for 9 months so he barely qualifies for this list but it was never Official so. He gets to be #1. On my first date with R he described himself as a "shaken baby" from growing up in NYC. He told me that once he got locked in his bathroom when he was a little kid, and he was stuck in there for under an hour but in that time he got so anxious he asked his mom to slide pictures of his family under the door so he wouldn't forget what they looked like. Aren't you sort of endeared by this functioning alcoholic stoner......? I was