I Hooked Up With One Of My Closest Friends. Now What?


This week’s edition of the Early 20s Mailbag raises two interesting questions.

One, what kind of slimy ne’er-do-wells are y’all hooking up with or dating? I can’t speak for #Lance, but I also have an unfortunate tendency to gravitate towards slimy ne’er-do-wells. So, I get it. But, at some point, enough is enough. Two, why is it still so challenging to effectively flirt? In theory, expressing interest should not be so difficult. In practice, it is a fine art that many of us fail to master. But, y’all, let’s make a collective attempt towards improvement.

Email us more questions, comments, or selfies! No one has emailed a selfie, and we are sorely disappointed.

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Q: I am a freshman in college and when I went back for break, I hooked up with one of my closest friends. It wasn’t weird at the time, but it was a little awkward afterwards. We ended up leaving to go back to school just a week later, so it was kind of perfect timing. When I go back home, we have a trip planned to Florida, just the two of us. How am I supposed to deal with the awkward tension, if there is any? The ride to Florida is supposed to take six hours and I am nervous about how he might act. Does he want to hook up with me again? I know I don’t, but this trip might end up in a state of intoxication — a state where I do not trust myself…at all. How do I go about handling this entire situation without ending it in regret?

Lance: First off, I wouldn’t trust myself in Florida either. Secondly, this is a totes brutes, yet certainly salvageable situation:

Being good friends will actually very much help your cause here — it means that the friends thing is the norm for your relationship, which means that you’re allowed to be completely honest with him without being unfair. So if you know you don’t want things to progress further, all you have to do is tell him — he might hate you, but he’ll get where you’re coming from.

If you do want things to progress, simply go with the flow and see what happens. Could end up being the best car ride of your life.

Steph: I hate how awkward people can become around one another when they have feelings for each other but don’t know how to express them. Ugh! Well, situations are only as awkward as you make them; this Florida trip might be the perfect opportunity to reestablish a normal friendship between the two of y’all — if that’s what you want. While y’all are stuck in a car together for six hours, take the opportunity to talk to him like you did before — as though nothing has changed because nothing has to change. And if y’all do happen to get a lil’ handsy like before, just vibe with it. You’ll both get nervous, awkward, or what-have-you if you over think what should just be a casual, fun situation.

Q: I just recently ended a 5-month long hook up, and when I say I, I definitely mean him. Long story short, we officially ended our non-relationship in December. He got back together with his long-term ex-girlfriend, and I just couldn’t find a good way to get over it. Come January, he told me he wanted to hook up with me again (while still being in a relationship), I was shocked. Mostly, because he told me his moral compass would never cross the cheating territory. Anyways, we hooked up. He decided he liked me again. Him and his girlfriend broke up (not clear on the reason), and we continued hooking up well into February…until he dropped me like a hot potato. He said things like “You’re leaving in May, so I just want to transition into friends.” and “I am really busy with school work this semester.” I decided to take it in stride, and agreed that it was probably for the best. However, last Saturday he texted me at 8 in the morning to come over for a casual hook up. Also, how do I stay strong when I catch myself missing him a lot of the time. Ugh, advice? Please? Need it/want it!

Steph: Honestly, this guy sounds like a schwald — a term my friend coined, which is similar in meaning to “schmuck” but exponentially sleazier (feel free to hereafter use it in conversation with friends). He strung you along while he had a girlfriend — which should be enough of a warning sign for you to keep your distance. Like, c’mon, cheating is a no-no, and he made you an accessory in handling his morally bankrupt sexual frustration. As if that weren’t already TM*, Schwaldy is still stringing you along. He chooses when he wants to come in and out of your life, dictates the boundaries of your relationship, and hits you up only when he feels like it.

It’s time to drop HIM like a hot potato. Even if he looks like, say, Andrew Garfield (trust me, babe, I would find that difficult as well), there are plenty of other players in the game. And they’re probably better at it.

*Short for “too much;” said loudly with each syllable slowly enunciated — to the point of obnoxiousness.

Lance: In all my years of writing world-changing articles like “16 crazy things you’ll do in college,” I’ve never heard of the 8am booty call. Truly unprecedented.

Thinking like the #bro that I sometimes am, he seems like he’s very immersed in experiencing every single hookup situation one could possibly experience — can’t necessarily fault him for that college mindset, but I’d let somebody else deal with it. He’s exhausting just to read about.

Q: I’m seeing this guy and he asked if I mind that he actually has a girlfriend. So we went underground and bluffed to everybody that we are just two very close friends. Meanwhile, we go out for dinners, watch movies and even having sex. Then one day, I found out that he married his girlfriend, from photos of his solemnisation ceremony uploaded on Facebook. I was devastated; I’ve never thought of forcing him to choose between me and his girlfriend, but now, I’m actually with a guy who has a wife. Even upon knowing that I was really sad and all, he didn’t do anything special to seek my understanding and could still behave like before. I know I should end this relationship but I am really truly happy when I’m with him. He understands me so well. Yet, I’m tired of being always the one to initiate for a meet-up, and I’m always the one to text him first(damn I couldn’t even last a morning when attempting to ignore all his texts!). I know I should let go of him but my heart says no. What should I do?

Steph: He has a wife. Stop right there. You shouldn’t be contacting him to meet up or hang out (or “hang out”) when he’s MARRIED. And, uh, remember how you found out he got MARRIED through Facebook, not because he had the decency to inform you? Listen, I am all for fluid love and open relationships, but it sounds as though his wife does not know you are his lil’ nug nug on the side. If he loves and understands you as much as you think he does, he would not be with her. Instead, he would spend his nights eating YOUR meatloaf, watching TV with his head in YOUR lap, and making YOU coffee in the morning.

Lance: That’s crazy. Much like people who write 2,000 word internet comments about 9-11 conspiracy theories, you gotta wonder where these people come from. I’d break up with him, just so that when you’re flipping through TV channels in 7 years, you can find him on a ridiculous, reputation-ruining reality show and not have to be involved.

Q: So, I first hooked up with this guy in my class a few weeks ago and a couple times since. We sit near each other and now every time he talks to me he’s an ass. He won’t have a normal conversation, he makes fun of me, and we’re in college so I mean, lets grow up. After class though he’ll text me and everything will be alright. What’s up with that?! I mentioned it to him and he told me I was being crazy and that he was in a ‘bitchy mood’, but it’s been happening for 2 weeks now and it’s getting old. What’s going on? Am I missing something?

Steph: You know when you were in third grade and expressing affection toward a crush entailed mocking them, calling them names, or sometimes putting gum in their hair (oopsies)? Back then, the key to seeming strategically disinterested and therefore ten times more attractive was acting cold and rude (eh, I guess that doesn’t change too much through the years). Most people mature out of such elementary school tactics, but your Boy-o sounds like he has not.

He sounds like he is somewhat interested in you but is too afraid (or awkward) to talk to you through a medium other than text — where potential rejection is less scary. It might be a good idea to leave him be until he can manage to start putting on his Big Boy Pants.

Lance: For some reason I just started picturing Lars, the dickish older brother of Twister from the terrific Nickelodeon show Rocket Power. What you’re describing is definitely how Lars would act towards towards girls.

Lars kinda sucked. I’d ditch him.