Emails We Can't Send At Middlebury

Heeeyyyyyy Thereeee Friend I Put On My Crush List And Subsequently Unexpectedly Hooked Up With,

Sooooooooooooooooo I think that drunkenly making out on grad night wasn’t the best way to say goodbye after four years. I swear I was trying to go for “lighthearted fun” and not “aggressively creepy” when I grabbed you and pulled you behind that mod.  Also, I have no idea what I said at the time JUST IN CASE I said anything vulnerable and remotely true - Remember, I WAS BLACKOUT!!!!!!

So even though we’re not really close friends (but have inevitably ended up in the same Milliken suite dozens of times), I want to tell you that I’ve really enjoyed our friendship! I want to let you know that you’re someone I would love to have in my life as a friend. A platonic friend. A very very platonic and special friend. Even though we were more than friends for a night WHICH I ALSO REALLY ENJOYED.

So I just WANT TO BE CLEAR that I haven’t been waiting all these years to jump you on the last night of school behind a modular home. I just want to maintain a friendship! As a friend! Even though you are exactly the kind of guy I would TOTALLY fall in love with anytime anyplace anywhere just say the word. But it’s cool and shit.

It’s the day after graduation. I haven’t slept ahhhhhh so this email might be totalllyyyyyyyyy crazy and spazzyyyyyyyy and make no sense at alllllllllllllll and I’m saying this just in case you never respond and I can blame this whole thing on my hangover!!

Cheers,

YOUR GENUINE FRIEND WHO SWEARS SHE HASN’T BEEN LUSTING AFTER YOU FOR YEARS BUT WOULD CONSIDER RELOCATING TO YOUR CITY IF YOU ASKED ME OUT ON A DATE

P.S. I know you were banging my friend during senior week. But it’s not a big deal!

DEAR SOPHOMORE BOY WHO THINKS HE DOESN’T HAVE FEELINGS FOR ME BUT JUST DOESN’T KNOW ME WELL ENOUGH YET,

Listen, I know how it is. You haven’t e-mailed me yet because you’re scared. I know this because I’m the bigger person. I’ve spent two more years than you at Middlebury and I also went abroad. To Europe. Which has taught me a lot about relationships and although I just came out of the closet and have never had a boyfriend, I think I have a lot to teach you.

First, I want to point out that you are probably struggling with your sexual orientation if you don’t have a crush on me. I have tattoos in all the right places, and my dimples dominate at least three threads on Midd Confessional. I have also hooked up with all of the girls you find attractive (or at least pretend to!) even though they thought it was ‘just for fun’ because they’ve known that I’m gay since the first time they met me in the J-Term Riddim Workshop freshman year.

When we hooked up four months ago, we lay on the floor of my room in my off-campus senior house and talked about love and life for almost two hours. I knew that we were meant for each other from that very moment. You asked me about my ironic Navajo dream-catchers, and my ironic posters of wolves.

We had both been members of club sports at Middlebury, which will surely boost our power-couple value when we finally start dating. We will be the hot, macho gays that everyone wants to have a threesome with, and that throw great dinner parties. I will cook the spiced turkey meatballs, and you will make sure that the Pandora radio was playing Annie Lennox station.

I don’t care if my friends hate you because I’ve told them you are a selfish, bad person. When you tell me that you were wrong, and that you love me and want me to inseminate your older sister with my sperm, and when you want to move to a quirky Boston suburb with me, I will tell them that you are actually an amazing man =)

I know this e-mail is pretty long, but I’m opening this dialogue because I believe in being the bigger person, and also don’t know what to write about for my sociology paper. I promise to stop sending you spiteful, confrontational text messages when I’m drunk, even though I will break this promise tonight. I was never very good at lent, despite what my huge cross tattoo might otherwise imply!

PLEASE REMEMBER that I typically kick people out after we hook up and generally don’t give a shit ever and I’m just pretty apathetic and collected.  Soon you’ll see that I’m kind of a hot jerk ;-)

Yours,

HOT SENIOR GAY WHO JUST CAME OUT OF THE CLOSET AND IS CRAZY AS A RESULT

Hey Melodramatic Senior Boy With Pseudo “Existential” Problems,

“I hate to send you an email as it can be easily misinterpreted, but you just sent me one and I have no idea how else to communicate with you since you don’t answer my calls.

I am coming out of a fairly complicated and waaaay too drawn-out situation with someone who kind of broke my heart, but who now is my “good friend” except once in a while we still have really serious talks to assure ourselves that we’ve retained some kind of special connection. 

Right now I just want to keep experiencing, whatever that may mean. I want to keep experiencing you. I just want to be. I just want to be in the moment. I just want to let ourselves be in the moment and see where the wind carries us. PLEASE SLEEP WITH ME.

To be honest, I am very attracted to you. I like the way you hold me in the morning, and I like the way you hum when you walk to the library, and the fact that you’re in an instrumental band. 

Here are a few simple and casual options I thought of off the top of my head:

 1. We can go back to the way we were when we were just friends blah blah blah you’ll feel like a good person and say “hi” to me.

2. You can JUST MAKE IT CLEAR THAT YOU WANT ME but without any rules or implications or expectations or understandings or guidelines or prerequisites!!!!!

3. You can decide you’re in love with me and totally blown away by who I am as a person and profess your love and take me on a date to the tea house.

Maybe you don’t know which of these you want, maybe it’s a combination of all three, maybe it’s just part of each of them, maybe it’s the first one, or the last one, or a few combined, or none at all. It doesn’t really matter. I’m pretty chill about the whole thing.

Call me whenever.

Or text. 

Or I’ll see you at dinner.

I might call you. 

I hope your break brings you peace and something else similarly spiritual that reiterates how mysterious and sensual I am.”

INTRIGUING JUNIOR FEB WHOSE FRIENDS ARE ALL IN EPIC RELATIONSHIPS AND JUST WANTS SOMETHING NON-COMMITTAL BEFORE SHE GOES ABROAD

Dear Seemingly Sensitive Sophomore Feb Boy,

“i’m sending you this email because i think you’ve sort of misinterpreted where i’m coming from… which is really disappointing because when i met you at crossroads café, i thought you seemed really sweet and it was cute how you flirted with me at that sng party in leatherworks, and then i found out that your brother is gay, and it was awesome.

so anyway, i think you’re misinterpreting. i was totally interested in a "casual” hookup, but i think i have a different idea of a hook up, a (more mature, sensitive, and generally much better) idea, though i value your opinion too (although you’ve kind of been a shithead, and avoided me all week, AND also, when the fuck do you eat dinner? it’s impossible to do a flirty run-in with you the dining hall, what the fuck.)

so here’s my perspective: i’m not super interested in sleeping with you after a dumb party in palmer and then having you leave immediately after. i don’t just want to talk to you when we’re awkwardly dancing to a live band at the mill, and i want to be relatively sure that we’ll hook up again, instead of worrying that i’ll end up eating a vegetarian quesadilla alone in grille at 1am.

 whats attractive to me about any kind of hook up is the potential for chemistry and some some kind of a emotion aka yes okay i’ve already imagined how we’ll fall in love and your gay brother will adore me and we’ll move to canada.

 but its ok if you were looking for something else. that’s ok! you’ve reminded me to be more a little bit more careful than to pursue a random sophomore who i’d mostly seen at the library, to maybe get to know someone better before making out with them in their hepburn double.

this really isn’t a big deal, really, despite the fact that this is an email and therefore “serious,” so don’t freak out, okay, just don’t freak out DON’T FREKA OUT.

i just thought you’d be a better person, mostly just because you spent a febmester “abroad,” which i thought means that you’re more, like, “earnest” or whatever, or at least a little more like wyatt orme.

you probably think i’m a crazy person. i’m not. i’m not. I’M NOT. i think that you are just immature. actually, you are 19, which is really young, a whole two years less than 21, which is my age. just so you know, next thursday night i will get really wasted at the bar, where you can not legally go, and i will look really hot, and i will dance in the basement, and also i will make out with my long-time, very smart, kind of bro-y crush, who already got a job in new york for next year.

see you around and when you do i will make sure i look like i have cooler friends than you!“

SLIGHTLY DESPERATE SENIOR GIRL WHO THINKS SHE IS BETTER THAN THIS