Letters to My Ex-Boyfriends

I had this plan to write a letter to each of my four ex-boyfriends and read them as ASMR. I’m posting them here instead because they came out a little bit sad and I don’t want to cry on camera. (It’s a waste because there’s no Oscars this year or whatever!)

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Dear Jake,

You are the only ex-boyfriend whose real name I am using for obvious reasons. When we dated freshman year for 3 months, I had to get a special dispensation from my mom because technically I was not supposed to have a boyfriend until I was 16. It was a short relationship but a very important one for obvious reasons.

I would like to set the record straight that you were in fact my first kiss, unlike the revisionist history I tried to perpetuate in the years following when I said that it was my neighbor who I met in confirmation class and used to talk to on instant messenger all the time. I did kiss him but it was well after you and I kissed and then he ended up kind of stalking me and scaring me a bit. Let the record show that my first kiss was with you in Craig Swidler’s basement.

I remember when you called my pink flip phone and I missed it and I knew you were calling to break up with me. I rang you back and we agreed we should stop dating and remain best friends. We both knew that January to March was just enough time for two fourteen year olds to “date.” Did we ever even go on a date?

Dating you was fundamentally important because now you’re my best friend who knows me better than anyone. Sometimes you tell me how I am feeling. You’re the only person in the world who can do that. You just did it the other day! (To anyone reading, wondering how a man could be so perceptive, he’s gay. Duh.)

If I was to truly write you a letter, it would be longer than this. I’ll probably send you a text longer than this in five minutes. Anyway, I would do anything for you.

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Dear High School Boyfriend,

Meeting you the fall of freshman year was so, so exciting. I will never forget that backyard party when I saw you and thought you were so hot and I forget which of your friends I told but they did amazing work with that information. Having a boyfriend who went to another school was iconic and you weren’t even bothered by the fact that I, at that time, was waiting until marriage to have sex.

Do you remember coming to my parents’ house to hang out with me after I got my tonsils removed? I smelled really bad and you sat with me and I think we watched a movie.

Over the course of our relationship, we got stoned and went to that sushi place at Goodwives Shopping Center maybe 100 times. Tengda! (That’s the name of the restaurant not a random outburst.) Every single time we went I got a Rainbow Roll with the special sauce (which I later found out is eel sauce mixed with spicy mayo, in case anyone is looking to try it at home).

For Valentine’s Day you took me to that really fancy place in Greenwich. I loved your Jeep and that we could make out in your room at your parents’ house. We had one playlist we would listen to over and over. We never got sick of kissing for hours to Animal Collective, “Wavin’ Flag” by K’naan, and “Pimpin’ All Over the World” by Ludacris. Still slaps.

Proms were fun. I feel guilty we didn’t really hook up after yours and it was because of me. I wasn’t in the mood! I had to catch a flight to Ireland the next day and I missed you so much while I was there. We had such a fun summer visiting the Block Island House and doing bad things in the outdoor shower. Thankfully for teenage us, the bible says you can do bad things you just can’t have P in V sex. When we broke up before college, I was ready. I thought a lot of fun experiences with guys were awaiting me at BC. That turned out to not be the case.

We ran into each other on Metro-North recently and awkwardly chatted the entire ride. Maybe we both would have preferred to wear headphones but I thought it was nice. Thank you for showing me what it felt like to be adored by a boy. I wish I had internalized more of how you treated me than how the boys before and after did. I think so highly of you and I am thankful we had each other when we did.

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Dear College Boyfriend,

I call you that but you were not in college when we dated, only I was. It’s taken me almost a decade to understand how dating a 26 year old when I was 19 profoundly shaped my view of relationship dynamics. I was fully in it and if anything I pursued you. I don’t feel like a victim I just wish I knew more then.

I had a crush on you since I was 14 and I was so excited when we started gchatting and Skype-ing after the New Years you spent visiting my brothers. I was in my college dorm and you were in your SoCal apartment. I’ve gone back and read those emails a couple of times and they are really sweet and sincere.

That first winter break I flew out to visit was so fucking exciting - we got to kiss for the first time after all of the build up. Looking back, I find it weird that no one said anything to me about the age difference. Not that I would’ve listened - probably just would’ve cited that I was mature for my age and done whatever I wanted anyway.

Going to Coachella with you and your friends in 2011 was very important for me personally even though some were very vocal that they did not want me to be there (since it was “Bro-chella” after all). And we missed Lauryn Hill performing which was the one artist I really wanted to see because you didn’t want the boys to be mad at you for ditching them. I really think you guys, as unfathomable as it sounds, wanted to see Duck Sauce instead.

If I hadn’t gone to Coachella and done LSD while watching Kanye West headline, I might never have dropped out of college. I can identify that as one of several turning points in my life. I still remember when he played one of the songs from My Beautiful Dark Twisted Fantasy and we sat down in the crowd and looked into each other’s eyes.

The good times were good and then the bad times were awful like

When you yelled at me for reminding your friend to collect money on her properties while we played Monopoly so I called you a psycho and you told me to pack my bags and almost sent me home… It wasn’t until recently, I realized that was the day I stopped liking board games.

When we were all drunk and the guys were peeing outside and you accused me of trying to look at our friend’s dick while he peed and were mad at me the whole night (I wasn’t looking at this dick but we did sleep together years later only once though)…

When you came to New York to visit after I dropped out of school and found out I shared a bed with my brother’s friend one drunken night, and even though nothing happened, you called me a slut, stormed out of the apartment, and threatened to fly home….

When you read my emails and Facebook messages where I told my friends in confidence I was feeling attracted to someone else and you called me while I was at work demanding answers…

I kept so much of this to myself when it happened because I didn’t want anyone getting mad at you. I knew that dating my brothers’ friend was a risk I was taking on and it shouldn’t be anyone else’s problem. I didn’t want them to think of you differently. We broke up Super Bowl weekend 2012 and I was sad that it ended but not sad it was over. I don’t regret losing my virginity to you because I did love you then and I felt safe and that you loved me back. Seeing you at my brother’s wedding was fine and cordial. I have no hard feelings toward you anymore and I just hope you’re okay and happy in your life.

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Dear Adult Boyfriend,

You know who you are! I want to start by saying I think you are a wonderful person and I am so thankful I was with you at such a crucial moment in my life (a moment being almost three years in this case). When you texted me the day after we first kissed, I was so surprised. I was sitting on the white couch in the Chinatown apartment watching TV and my phone lit up. We were so drunk and stayed up the whole night. I was in a fog but looking down at my phone, I was smiling.

It was a couple of months and a few fumbles before we started dating.

That one night we hooked up after a work happy hour and I left because you fell asleep and yes the candles were still burning because I was also drunk and forgot to blow them out…

The weekend you went to a bachelor party and when you got back you were showing me photos on your phone and accidentally showed me one of you kissing another girl and told me it was someone else but I said that’s your shirt so you came clean…

Those were silly little things before we got serious and our lives became deeply intertwined. We worked at the same place and you were one of my brothers’ best friends (you might say that’s an old habit of mine). I was so in love with you I downloaded The Bleacher Report so I could read about college football! I did ski school! I hung out with dogs!

You taught me how to be a really good girlfriend. You did not teach me how to be a really good partner. it wasn’t your fault at all that at 22, I had no sense of self.

When we moved in together, it made perfect sense and I thought we were going to get married. We had a really nice life between New York, Connecticut, and Vermont. You made me feel so safe and secure. Thank you for being there for me when I had an anxiety attack about my parents’ dying, brought on by that last season of Mad Men.

It was because of how confident I was in our relationship, as your girlfriend, that I looked outside of it for something new. That’s when I found comedy. I would’ve never done that if I didn’t know that I had your support always if it didn’t work out. That was what led to the end of our relationship but I think it really just pointed out some of the flaws we had been choosing to ignore. I didn’t actually want you to die in an avalanche, I just wanted to break up.

I’ve been so happy to watch you flourish and thrive in your new relationship and I wish you a very happy marriage. I genuinely feel lucky to have dated you in my early 20s before I had come into my own. In the years since, I have begun to understand how much being with you, especially toward the end, informed who I became in the years after.

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I think four boyfriends is enough for one lifetime. Change my mind!