All The Boyfriends I’ve Ever Had in Chronological Order, Pt. 3 of 4

Dave 1996-97

Dave was the boy I consider to be my first real boyfriend. He’s a perfect example of “persistence beats resistance,” in that I obsessively pursued him until he broke down and made out with me. It sounds worse than it actually was but that’s the gist of it. One night we all slept at our friend’s house and him and I slept on the couch. At first only our feet were touching. We were both pretending to be asleep but not really. We ended up making out all night “in our sleep” and I felt high. I drove home at 6am and wasn’t even tired.

When Dave was my boyfriend, I started to understand what the whole thing was really about, which is, more or less, having someone to always hang out with. I’d say sex plays a big role as well but this was not the case with Dave. Dave was my first but I wasn’t his. Maybe he felt creepy about that, but either way, I think he felt like he had to be very gentle and responsible with me, which led to a lot of anticipation. Then one night, we finally went for it. Or at least tried to. I really don’t think his dick got very far before I started screaming in pain. Have you ever lost your virginity? Shit fucking hurts balls! Dave was actually a great boyfriend. He was patient, considerate, funny, cool, and made me amazing mix tapes. We had a lot of fun together and even though he was sXe, he didn’t mind that I did drugs. Dave was the best first real boyfriend a girl could have, but soon I was growing up and moving on and I wanted to see if sex would hurt less with someone new. I went to college.

Jake 1998

I was almost gonna transfer, and I would’ve too if it wasn’t for Jake.  My entire 1st year of college I was a fat fag-hag. I gained weight, wore really baggy pants, smoked a ton of pot and made fun of people with my gay BFF, Tim. It was a really good time, but not a great strategy for getting laid. Tim told me he was transferring to NYU and because he was my only friend, I wanted to also. Then the weather started getting warm. I was in Massachusetts where the winters are long and cold and college kids are fat and pale, but when the sun comes out… holy shit. It was like a human fuck fest. I actually started going to parties. Like older kid parties. With girlfriends that became my “wing men.” And since we were the new hot little babes that no one had known all winter, Jake liked me. He was very small and thin and pale and had glasses and wore the same shirt many days in a row. He was the first person I ever met who celebrated his own alcoholism. I didn’t know that was a thing that could “rule” so hard but then again, we were college kids. It is a time of learning things and saying dumb things and thinking they sound smart. A wonderful time. The best time. One smart thing I realized was that if I got really drunk, sex didn’t hurt so much. So that happened. I felt cool with Jake because he was older and indie and I was getting accepted with the indie kids. Then school ended and Jake wrote me letters from Detroit but they were longwinded and I had other plans. No time for letter writing when there are drinks to be drunk and a newfound lust for lust.

Brad 1999 (?)

Was Brad my next boyfriend? Methinks yes. I liked him all year at college but supposedly he had a pill addiction and didn’t leave his room that much. Not until the weather got nice again. We hooked up but he said he didn’t want a girlfriend he just wanted to be “best friends.” I said okay to that. We hung out a lot and went food shopping and everything but stopped making out. Then I made out with one of his housemates and he got jealous and decided he wanted to be my boyfriend, which I also said okay to.  I really liked him. I was definitely way more into being his girlfriend then he was into being my boyfriend, and I sort of knew it but ignored it. He graduated and I felt so proud. He said he wanted to move to Chicago and I was like, but I live in New York? I didn’t get it. He came to New York to visit and stayed with me one night on my sister’s couch.  When we woke up, I walked him to the subway and he said he’d call me later to go 80s dancing. I said, “cool” and felt happy. That was the last time I ever saw him. Thought Catalog Logo Mark

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