All The Boyfriends I’ve Ever Had in Chronological Order


Gabe – Circa The Early 80s

Gabe was my boyfriend before I knew what a boyfriend was. I was in my late 6’s and early 7’s. He was a year older then me, which was a big deal at the time. He was small for his age and bossy, but funny.  Once he said “I got bit by a red ant,” and Wayne Goldberg was like “Did you die?” We laughed really hard about that. He picked me first to be on his team for games like tag, and when I got called “out” he would always make an exception. When it rained we played hide and seek in his basement.  We hid in the closet together, turned off the lights and kissed. I remember being able to see the whites of his tiny teeth. When he got the chicken pox my mom let us hang out, hoping I would get the chicken pox too so I could just get them over with. We sat on his driveway and traded Star Wars cards. He gave me Princess Leia and the Ewoks (obviously). His house smelled like suntan lotion. His family took limos to the airport. He was the first friend I ever had who was always on my side. This was before he realized that it wasn’t cool to like girls, which shortly followed. His family moved away to another neighborhood very close to mine, but to keep hanging out after the move we somehow realized was too intense. We stopped playing together and I took to dance routines in the backyard while he took to BMXing with the boys. In high school he asked me if I remembered when we used to kiss in the closet, and I lied and said “no.” He said “I knew you would say you that.” I don’t know why I lied about it. It just came out of my mouth that way before I could stop it.

Eric – Summer of 1987

At camp every girl had a boyfriend. It didn’t matter how old you were or what you looked like. It was just a thing that went down.  We called it “going out.” I thought Eric was cute and for weeks I would stare at him during “line-up.” Line-up was when the camp gathered once in the morning and once at night to go over things. It was like a community meeting. For weeks Eric and I would look at each other and then look away. It was the first time I ever participated in this kind of mating ritual. Look at him, look away, look at him again. It made my heart stop and start over and over and I realized I loved that feeling. From the moment I woke up it was the first thing I thought about. Whenever there was a chance of any kind of interaction with the boys, during meals or just walking to the next activity, I would look for him to make eye contact and get that feeling. It made me feel high. Then one day he asked me out, or a friend of his asked me out for him, which was a popular way to do it at the time. I said yes. I didn’t know what I was supposed to do with him once we were “going out.” I had never thought that far about it and I was scared shitless. The minute I realized I had to talk to him, the exciting feeling I had went away. It was like poof, instead of turning into a pumpkin at midnight, I just turned back into a regular girl with underdeveloped hormones who loved candy and stickers, not boys. We walked around the lake together while people were watching. I had a necklace made of seashells on and the whole time I just played with the necklace and looked down at my feet. I don’t remember saying one word to him. “Going out” actually sucked. When we got back from walking around the lake I told my friend to tell him that I didn’t want to “go out” anymore. I’m pretty sure he was upset, but I felt relieved.

Toby – 4th Grade, 1988

I was best friends with two girls: Tiffany and Stacy. We were all in the same class. Two boys, also in our class, Loren and Jeff, lived in my neighborhood. Jeff liked Tiffany and Loren liked Stacy. The boy who liked me was Toby. Toby had red hair and did not live in my neighborhood. He didn’t even live in Woodbury, but Syosset, right next to the school. Toby was a grade older than me and wrote me little notes everyday. It was overwhelming but he was cute and popular and was actually a grade older. One time his note said, “I really like your ponytail today,” when my hair was actually in a French braid. He would always add a PS at the end that asked questions such as “PS do you like Def Leppard?” And he’d write it in the Def Leppard font. His head would pop up in the small square window on the door of my classroom, which, according to one of his notes, meant I was supposed to ask if I could use the bathroom and then meet him in the hall. At first I found this exciting but after the 3rd or 4th time, not so much. The other boys, Loren and Jeff, were a little scared of Toby but since we were all best friends, they’d be forced to hang out. Everyone got quiet when Toby was around because he was older and would curse a lot and say words like “pussy.” Once we all went to the movies and Toby was throwing popcorn and acting a little too wild, but then he calmed down. It actually turned out to be a fun night. I feel like we saw that movie “Hiding Out” with Jon Cryer but I could be wrong. After the movie Jeff’s mom picked us up and we all went back to Jeff’s house. I remember thinking that Jeff and his mother looked a lot like ALF. We played spin the bottle and I made the mistake of kissing Toby on the lips. After that night all he wanted to do was kiss me on the lips. In school, every hour, he would pop his head into the small window and I’d see his orange spiky hair bobbing, motioning for me to come out. I would ignore it. I didn’t feel good about this but I also didn’t want to get in trouble and I didn’t want to kiss either. Kissing got boring fast and I felt really, really overwhelmed. I dumped Toby and he was FURIOUS and started being really mean to me during school days. I felt really upset and cried because he was being so mean and getting some older girls to be mean to me as well. When he heard I cried he wrote me a note that said “I’m sorry and I’d really like to be friends, maybe even get back together one day.” I said that sounded like a good idea even though I had no intention of that ever happening. I did however, consider revisiting Toby in Junior High when I realized how cool he was, but by then it was too late.

Mike F – 1990

All of the elementary schools in Syosset and Woodbury had finally conjoined only to form one very unattractive junior high school. This meant new girls to hate and new boys to like. I liked Mike F.

Short, obnoxious, bad grades, hyperactive, liked hockey. He was a little Italian fucker. Word got out that I liked him (which was true, even though I had never spoken to him) and so he asked me out via folded up 1000 times note on yellow loose leaf paper. I said yes.

I felt weird about it because we had never actually spoken. I even saw him in the hallway once and didn’t say hi. He saw me too. It was one of those awful moments where you both see each other, you both know, and you both ignore.

We were doomed.

I don’t remember how it ended, but it didn’t last longer than two weeks, tops. I count Mike F. as a boyfriend only because for the next three years of junior high I really didn’t get much play. Him and I ended up becoming friends because he was the class clown, and everyone wants to be friends with the class clown.

Kris – 1991 or 1992

He was THE WORST BOY IN THE ENTIRE SCHOOL DISTRICT. He was always getting kicked out of different schools. He was always given “2nd and 3rd chances.” He came from a family of boys where each one was worse than the other, and even his parents were bad too. It was like an “O’Doyle Rules!” type of family except they didn’t rule. Well, sort of, because we were scared of them. The oldest brother was the hot one, Steven. Marcie gave him a BJ and then Hali beat her up. TROUBLE.

Kris was the shorter one who was somewhat chubby. I had seen him at the Broadway mall with Toby (see part 1) and thought he was cute. Plus I was getting sick of not liking anyone. I was so bored. All of my friends were growing boobs except me. I needed something. Kris was my second French kiss. He was really cute about it. These were during the days when hanging out at the skating rink was a “thing.” We kissed at the skating rink and felt a little less shy around each other afterwards. He would call me on the phone after 10pm, which was not cool at my house. My mom would always pick up after I had answered and be like “Who’s calling so late?” and then Kris would imitate her voice and make fun of me for not hating my parents.

He told me over the phone that was I flat chested, which I knew, but come on! I dumped him. He ended up being the #1 pot dealer in all of Syosset. (If he reads this he will probably kill me).

Ben – 1994

I wasn’t attractive to boys for most of my life, so there were a lot of years when I mostly just had crushes. Crushes don’t count as boyfriends. I liked Ben and I had seen him at hardcore shows. His best friend did a zine so I jimmy rigged my way in with Ben by writing for this zine. Wouldn’t be the first time I jimmy rigged a boyfriend via writing, and it wouldn’t be the last.

Now that I think about it, I’m pretty sure Ben did not consider us boyfriend-girlfriend, but we talked on the phone every night and hung out together on the weekends. He played the drums (still does) and was really into Slint and Drive Like Jehu, two indie bands that girls don’t really like. We went to see Pulp Fiction and held hands, and later that night kissed under a blanket in his brother’s room. We never officially broke up because we were never officially going out. I think I had heard a rumor that he liked another girl. I was “appalled.” I pretended to be bummed for a day or something and then I realized I hadn’t liked him all that much anyway, and went back to obsessing over someone else.

During this period of my life the only reason I had to live was the idea that I would one day have a boyfriend. It was what got me out of bed in the morning, what made me put on an outfit. I completely lived in fantasy 95% of the day. You know that thing when you have to wake up for school or work and it’s so hard to get out of bed, so you focus on that one good thing—it could be anything: a new pair of shoes or the movie version of Romeo and Juliet you’re watching in English (Leonardo DiCaprio version). For me, most of the time it was just a guy I had a crush on, and the fantasy of that guy falling in love with me. What would I wear that day to make him notice me? What route would I take to my class so I could “accidentally” bump into him? Sadly a lot of this behavior kept me away from having a boyfriend rather than just being myself and maybe having one. Or maybe not having one and being fine with that. It was around this time that I started writing a lot of poetry.

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.

Kevin- 1999-2000

I loved Kevin. From the first moment I saw him I loved him. He was wearing khakis and a green windbreaker and had a slight case of acne. Swoon alert! I asked around Hampshire, “Who’s that kid in the green windbreaker?” His best friend, a former heroin-addicted lesbian, had just moved into our house so Kevin started coming over all the time. I high fived myself in my brain. He would walk into the house and rush by us because we were an intimidating bunch and I’m sure I was always staring at him. I told my lesbian housemate that I thought her friend was hot and the next thing I know the three of us are taking bong hits in my bedroom. I went to put on music to make things less awkward. “Should we listen to The Pixies?” I asked, but Kevin didn’t know who they were. Double swoon! He told me he was in the chess club and majored in math. TRIPLE SWOON. Kevin was funny and awesome and we become a good couple. Or so I thought anyway. He sold pot and we both smoked it by the truckload. Then we discovered heavier drugs together. It all went downhill from there. It wasn’t that we fought or didn’t have good sex. We were best friends. The problem wasn’t our relationship, it was us. We were young, dumb, co-dependent, and heroin addicts. The drug made everything weird because it always came first. I feel sad when I think about Kevin because it was the beginning of something so awesome and innocent and just turned dark and awful. We both eventually cleaned up but to this day he won’t talk to me for whatever reason. Maybe I did something bad. Maybe it was all my fault? I’m sure he’s killing it wherever he is. He was a good one.


This poor guy. Extremely good looking but quiet and dorky and reserved. I dropped a bomb onto his world when I met him in New York City and introduced him to heroin. I’m not even sure what he was more addicted to, the drug or me. I swore up and down that I loved him but what I really loved was his reliability. I loved having someone to get high with and snuggle with. I never wanted to be alone. I ache when I think of these days. I was scared of everything but was still too young to know how to admit it. Craig played guitar and keyboard and also key-tar. We sang songs together and got high and even drove across the country. What did we talk about? I’ll never know. We listened to Harry Potter audio books. He was with me when 9-11 happened. I can’t even remember either of us reacting to anything. At least it was drama free. One night he was sleeping in my bedroom and I was in the living room with another guy, giving the other guy a BJ. WHAT? Who was I? I was 21 or something. I thought everything was soooo important and I was soooo in love. How certain I was of it. Fuckin’ a. I wish I could go back in time and punch myself. I can’t even remember how I broke up with Craig. Oh yeah, I went to rehab.


James was my first sober boyfriend. He wasn’t sober, but I was, so in a way it was like dating one of my first ever boyfriends (see part 1). James and I moved into together immediately. He would whine all the time about how cold his apartment in Brooklyn was and this was around the time the feeling of guilt first entered my relationships, so I felt it was my duty as a girlfriend to have him live with me. Stupid. He moved in and I got a second cat and we stopped having sex, in that order. I started to resent James because a) he was a bit of a liar and b) he was afraid of me. He smoked a shit ton of weed and laughed even when things weren’t funny. That’s the worst isn’t it? I broke up with James after 8 or 9 months when I met someone else who was funny and awesome and was just my best friend (it was a guy, yes). I was like, “Oh wait, this is what I want. Someone awesome rather than someone boring and shitty.” I broke up with James and he threw a remote control at me. Then I told him I was going to Long Island for the weekend and that his things should be gone when I returned. I left the apartment but ended up missing my train to Long Island so I turned around and came back. I sat around, smoked a cigarette, checked my email, made some tea, and suddenly I heard someone in the bathroom. I got scared. “Hello?! Who’s there?” James appeared from the bathroom where he had been hiding in the shower. WTF!?! I was all, “Uh… were you hiding in there this whole time?” And he was like, “Yeah,” and nervously laughed. I felt weird, but I also didn’t feel guilty and was glad to break up with him. He’s actually a really nice person. Sorry?


My list of boyfriends has to stop here because I’ve been asked by several current ex’s to not include them. After James I went out with 3 more guys and now I’m on my 4th and hopefully last. The end.