How To (Finally) Have Sex With Your Best Friend

How To (Finally) Have Sex With Your Best Friend

You’ll become fast friends before meeting each other in real life.

You’ll begin exchanging messages online months before her family finishes building a large log cabin in your school district, forcing her and her siblings to transfer to a place they never wanted to be.

Another female friend will have met her at volleyball camp and come to the decision she should get to know you because she thinks you would be a good couple, insofar as two adolescents can truly be a couple.

(They can. The feelings are real, though individually unprecedented, raw and misunderstood. The first few times you catch legit feelings will mold the way you digest and address them in later years. And you’ll never forget those firsts — no matter how much you may end up desperately wanting to.)

The first time you’ll lay actual eyes on her is on the first day of the science class you’ll have together. She’ll be pretty. You’ll wonder what it must be like to have to uproot your educational and social life at a better public school closer to the city in exchange for a more rural place where you know next to no one and are wary (for good reason) at the quality of education you’re liable to receive. It must be horrifying and upsetting. Luckily, she’ll play soccer and it’ll help her get to know others in that way, so she’s not a complete stranger to the in-school society.

You’ll become the kind of friends who instant message back and forth for hours on end.

There’s an attraction there but it will take you a while to act on it.

About a year after you meet, you’ll become something more.

She will become your girlfriend. You will become her boyfriend. It will last about one month.

There will be only one date, when your respective parents drop you off at the movie theater.

You’ll call it off and ask to be friends again. It is unclear why you will make this decision.

Later on in life you’ll find yourself wondering when your commitment phobia officially began and conclude that maybe it has been a part of you forever, for reasons you can’t understand. You’ll consider seeking therapy and taking other measures to find out, in an effort to hopefully not die alone.

The specific trigger, if there ever was one, will likely take a while to uncover. And you’ll be afraid of what you might find out.

Also, at the time, you’ll behave like a prick, generally. You’ll make horrible decisions, decisions that seem rather insignificant at the time but then will tend to haunt you for years or even decades.

It won’t be long at all until she’s wooed by a dude two years older than you. You’ll immediately become jealous of their relationship and talk shit on it to her at pretty much any available opportunity, though you’ll know full-well you have had your chance and are just being bitter and petulant.

Eventually, you’ll stop making your remarks. Their relationship is a healthy and loving one and if it were to end and you were to somehow rekindle a romance with her, you’d probably fuck it up anyway, probably via self-sabotage. Like you always seem to do.

But you’ll remain friends. Close ones. Best friends. The whole way through high school. At some point after her boyfriend graduates and enters the military, they’ll break up, kind of, though not completely. It’ll be mostly unclear what they are but you’ll suppose after a few years together it’s difficult to just completely call it quits. At this point, you’ll still be holding a candle for her, but she doesn’t know this and you won’t do anything about it.

You’ll both graduate.

You’ll both go to college. She to Penn State’s main campus in the middle of the state, and you to a branch campus as far northeast in the state as one can really go without crossing into another.

There won’t be as much communication as you adapt to your new lives, but you’ll think about her often, even as you’re spending most of your time trying to get other women on your campus to think about you.

You’ll go nearly the entire semester without seeing her, but then you’ll quit basketball and have your weekends free, so you’ll go to visit her campus a couple weeks before Christmas, the weekend before finals.

You’ll arrive on a Friday evening after a four-hour drive, just in time for your friend’s holiday party to begin at his off-campus apartment. Freshmen don’t usually live off-campus, but he’ll live with his brother who is of legal drinking age and willing to buy plenty of booze for minors, which is pretty clutch. She and her friends will be coming to this party.

You won’t realize just how nervous you are to see her until she texts you their ETA, at which point you’ll almost vomit but also feel very excited, elated. Your butthole will clench a little bit.

She’ll walk into the party with some friends from her dorm floor close behind, all scantily clad. She’ll be wearing a red tank top and black leggings, and look absolutely amazing. You’ll think, God, I’ve missed her freckles and her smile and her laugh and all that other amazing shit.

The two of you will catch up on a couch while drinking jungle juice and anything else you can get your hands on. At one point you’ll take a shot of Everclear grain alcohol.

Immediately afterward a friend will show you how it can remove the staining from the coffee table. This may seem like cause for alarm, but it’s already in your body, so what are you going to do? It’s a good thing she will have passed on it, because she is approximately one-half your size.

You’ll tell her that you’ve missed her. You’ll tell her that since you’ve quit the basketball team, there’s no reason for you to remain at the branch campus, and that you’ll be transferring the next year or the year after.

You’ll want nothing more than to kiss her, but know you will not try to do so, because a true friendship sustained is better than one damaged by a non-mutual attraction (maybe, possibly, probably, who really knows?). One made forever awkward when one party exposes his or her feelings only to find out they’re not mutual or reciprocated. You’ll reason you would rather have her in your life as a friend than to not have her in your life at all.

The two of you will talk and talk and she’ll touch you in affectionate ways, ways that might be more-than-lifelong-friends affection but you’ll tell yourself that’s just your imagination, just your indulging in a little bit of holiday hope.

You’ll try not to think about the two of you as a couple, an “us,” celebrating Christmas together. Your trying not to think about it won’t work, will probably make you think about it even more.

You’ll go into the kitchen to do a group shot and then go to take a piss. You’ll try your best to point it at the pool and sprinkle out some urine without spraying it all over the bathroom.

She’ll be waiting for you when you come out of the restroom. You’ll smile at each other.

She’ll grab your hand and lead you into one of the bedrooms, where she’ll initiate an aggressive makeout session.

You’ll leave the room together, only to return moments later. This time she’ll push you onto the bed. There’s a moment where you’ll wonder if she’s planned this or if it’s spontaneous, if she truly wants you or if you could be anybody else, just someone not her pseudo-ex-boyfriend to really solidify their still not complete split. You’ll decide to just live in the moment.

If I am being used, fuck it — I’m fine with that. I think, you’ll think.

She’ll say, “We should leave,” and take you back to her dorm on a bus that runs a route called the White Loop. You’ll hold hands and kiss on the bus, not caring in your drunkenness about the obnoxious nature of public displays of affection.

In her room, on her twin bed, you’ll undress each other, drunkenly, and when you’re both naked she’ll say, “Should we do it?”

“What do you think?” I ask.

She’ll looks you in the eye, nibble on her lip (you’ll almost come right then, really), say, “Let’s do it.”

You’ll jump off the bed, rifle through your pants until you find your wallet and the condom inside, hoping she won’t change her mind and that you won’t completely embarrass yourself — though you have learned some things since the last time you were around her when she didn’t have her pants on. (This time John Mayer’s “Your Body is a Wonderland” will not be playing in the background.) Also, this time you’ll be drunk, which you’ve recently found really helps with longevity.

While she’s on top of you, she’ll say, “I’m pretty tired. I think we should go to bed now.”

She’ll fall asleep soundly almost immediately, her head resting in the crook of your neck. Her hair will smell nice. She’ll smell nice. You’ll want to be in bed with her always. She’ll be pretty even when she sleeps. You’ll feel vaguely weird watching her sleep, but will also be too excited to drift off.

My life as I know it may have just changed forever, you’ll think.

It’ll seem melodramatic, and it probably is, but whatever.

Finally, you’ll pass out.

The next morning you will wake up early and she’ll walk you downstairs. You’ll kiss goodbye after a brief conversation about seeing her again before you leave the next day.

It’ll be cold out and you won’t be wearing a coat, not having thought to put one on on your way out the previous night, but you won’t care.

You’ll walk the two or so miles back to your friend’s apartment, smiling like an idiot the entire way.

You’ll stop and buy donuts and coffee for your friends, who greet you with congratulations and a unanimous “It’s about time.” You haven’t told them about your attraction to and maybe even love for her, but they know you well and will have sensed it. You will not be as opaque as you think you are.

You’ll text her to see what she’s doing that night and she’ll say she’s not going to go out, because of finals, but that maybe the two of you can have breakfast before you leave the next day.

You’ll immediately want to respond and ask if you can bring her anything to help study or whatever, but know this would be a bad move, that you would seem too desperate to see her again. You’ll also want to ask her if she only did what she did with you because of her drunkenness, but you’ll be petrified at the mere prospect of how that conversation might go.

The next morning she tells you her kind-of ex is coming to visit her and she needs to see him.

You’ll travel back to school despondent and try to distract yourself by focusing on finals.

It won’t work too well.

You will not speak of the sex for some time. She’ll continue to see the kind-of ex on-and-off for a while, and you’ll try to move on.

When things end with him, finally, she won’t be single for long. She’s a relationship person. She’ll have a boyfriend for most of college, a guy who will become a friend of yours.

It will become clear that she doesn’t want to be anything more than a friend, and that that’s all the two of you will ever be.

She’ll even hook you up with some of her friends, and you’ll take advantage of it. You won’t know if this makes things better or worse for you. But it feels good physically, and if she won’t want you it’s nice that somebody else will.

Eventually, at a friend’s wedding, she’ll bring up the one night together.

You’ll be her date at the wedding, but mostly because her boyfriend won’t be able to make it, or is unwilling to come.

She’ll tell you you helped liberate her from the high school boyfriend, the guy who took her virginity. She’ll say you made her realize there was more out there. More to explore. More to experience. More fun. More beauty. Etc.

You’ll wonder if you’ll ever stop wondering why you never told her how you felt. This will persist as she dates more guys, as she finds one who will stick, who will become her husband.

She’ll invite you to the wedding, last minute, but you won’t go.

She’ll have a kid. Then another.

Still, you’ll wonder.

The only thing that will calm it is going out and doing what she did.

You’ll try to find a friend first.

You’ll try to find more.

When maybe what you once had was already more than enough.

This piece was previously published by PS I Love You. Relationships Now.

About the author
Scott is a writer and journalist who lives in Brooklyn. He thanks you for reading his stuff, and you can get in touch ... Follow Scott on Twitter or read more articles from Scott on Thought Catalog.

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