Questions From The Chase: Drunkenly Hooking Up With A Friend, Self-Sabotage, & Long Distance

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Hooking up with someone new is usually pretty fun. There’s a nice little mix of anxiety and excitement, but when you end up having sex with someone who’s been your friend for a long time the anxiety about what happens after it’s over is downright frightening. Waking up after a blackout and only having faint memories of how you ended up in bed with another person is not ideal.

This week, we’ve got a question from a girl who seems to have put herself in a very precarious situation. It’s in quotes below and as always, keep the questions coming my way.

I woke up this morning, still drunk and someone in my bed. I never allow sleepovers. Then I was hit a wave of some very fuzzy memories from last night. The guy next to me in bed, also naked, is one of my best friends. We’ve known each other for six years, and last night we fucked. I can carry on like nothing happened, but I don’t think he will just brush it aside. Have you drunkenly hooked up with any good friends? What do I do to make sure this doesn’t change things?

First off, let me just say that I’m with you on the not allowing sleepovers thing. Sleeping alone is awesome. You get to spread out. There isn’t another human trying to steal covers or the best pillow away from you. This is a royal pickle you’ve put yourself in.

For the most part, my last two years of college are a blur. I made a lot of lifelong friends over half gallons of Canada House whiskey and tall boys of Busch Light. Some of those friends happen to be girls. So when I drunkenly hooked up with one of those girls last summer, it was understood that we would never mention it to anyone or to each other for the rest of time. What can I say, sometimes little head wins over big head. She tried bringing it up once at a bar a few months ago and I brushed it aside quickly and made a bee-line for the bathroom to avoid talking about it. It was awkward, and it still is when I think about. We’ve been friends for close to three years now. So I can’t imagine what you’re going through with a friend of SIX YEARS. It sounds like he has a crush on you but you tossed him in the friend zone a looooooong time ago.

Before I get down to the nitty-gritty, I have to say, good on this kid for finally making it happen. Having sex with you has probably been on his to-do list since you guys met six years ago. I know that there is a school of thought out there that says any guy who is friends with a girl is only friends with her because he’s trying to do her. It’s flawed logic because I do have girl friends who I would never in a million years try to bone. But there is an inkling of truth to it.

But you’ve put yourself in a position that’s going to be tough to get out of. Nobody likes sitting people down to have serious discussions. It’s nerve racking and you’re going to have to draw a line in the sand. You have to let this guy know it’s not going to happen again and that if he wants to stay friends, he’s going to have to respect the fact that you don’t want to have sex with him anymore. It’s easier said than done. I don’t envy you in any way. But you have to be harsh. Be blunt.

Make sure the message sticks because the last thing you want is this guy getting into sad Drake music and drunk dialing you crying every night begging for a chance to “make this work.” He’ll probably use the phrase “getting on board with the idea” as well. Let me know how it goes, I’m dying to hear how he takes this. My guess is not well.

I know that you are beyond tired of girls who come to you with the attitude that “omg I’m gonna be single forever” but I genuinely feel like I’m gonna be single for fucking forever. I’m a 20 something girl who’s addicted to the chase. Every guy I meet, the second I get bored, I fly the coop. If I know he’s interested, byeeeee. Dating apps are another story. I’ve had a fair amount of dates–nothing. I want commitment but when anyone gives me the vibe that they wanna settle down, I’m outey. Help. I live in Nashville. Grew up here. I’m more than just averagely attractive, I’m in shape, I have an ass that doesn’t quit. I can make anyone laugh. There’s no real reason I should be single. Don’t get me wrong, I’ve been in relationships before, healthy ones that just did their time. I’m the relationship type person but maybe I’m too independently minded and that intimidates the opposite sex. Need your wisdom, champ.

So you allegedly have an ass that doesn’t quit and you live in Nashville which is supposed to be an awesome city to live in. Anytime someone tells me a story about their trip to Nashville, it ends in debauchery and an ill-advised trip to one of the million strip clubs that town lays claim to. I think you answered your own question, though.

You’re a twenty-something girl in a sprawling metropolis. Chill the fuck out with your prognostication that you’re going to be single “for fucking forever.” You said that you’re someone who shies away from commitment the second a guy shows interest in you. If that’s true, you must be incredibly annoying and frustrating for guys. Do you realize how confusing that is for the guys you’re seeing? All we ever hear is that girls need attention. They need to feel wanted. So you’re complaining about not having a boyfriend but you’re the reason you don’t have one. The self-sabotage needs to stop. If you want a boyfriend as badly as you make it seem, then stop acting like a goddamn lunatic.

Girl who moved out of town comes back to visit, and whenever that happens it turns into an event. She is really close to me and my usual crew of hooligans, but she has a huge circle in the city outside of us. Needless to say she has a stable of beautiful friends, but the only time they come around is when she is with us. Well last time she came into town, the few survivors ended up at my place for late night. One of the said beautiful women ended up in my bed, and you know the rest of that story. While I have a certain amount of self confidence when it comes to my looks, I know what my wheel house is. She was definitely a step above. And since there were a number of people who stayed at my place that night, there wasn’t much opportunity to gauge her vibes the next morning when we took everyone back to their cars. The extra layer to the question is that she lives a solid 30 minutes outside the city, so any plans to hang out are a rather direct request. The whole meet up while out option isn’t really on the table. So while I have no issue putting off the direct vibe, I really can’t read if that night was more a product of right place right time, or if she is down to clown again. And even if it is purely physical on her end, I don’t want to scare her off with getting to formal with dates etc. So even when while she ended up in my bed, the only real time we had alone was with the lights off. So reading the situation is proving difficult. We exchange a few texts and are on each other’s short list for snap chat recipients, but that is really all I have to go off of.

Sounds like you’re outkicking your coverage here, my man. Congratulations on the sex. Sex is dope. Honestly, I’d say it’s probably worth it to explore dating her. If she’s as hot as you say, living thirty minutes away from you is do-able.

As an aside, I’d really like to call Snapchat out for a moment. That company needs to bring the function that let people see your top 3. No easier way to figure out who’s fucking and who isn’t. I say ask her out on a date. Worst case scenario, she says no and it’s not like you’d see her out at the bars you frequent anyway. I don’t know how crazy you’re feeling, but I’d go for the away game. Suggest a spot in her neck of the woods, put your hardhat on and go to work. Adds a little drama to the situation and she’ll probably appreciate the fact that you’re willing to drive out of your way to see her. .

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Johnny D

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