We all know that hooking up isn’t all rose petals and follow-up phone calls. In fact, more often than not, the morning can be excruciatingly awkward. Sometimes, that awkwardness follows you down your walk of shame, and lingers like a black cloud over your relationship history.
You might be able to laugh off some of these poor decisions, but in other cases, you might reap the consequences, especially if your fling affects the people around you. Here are some awkward hook up scenarios that you may just wish to avoid in the future.
1. Your Best Friend’s Brother.
Usually, you give your best friend all of the deets regarding your trysts, and she listens, and laughs, and offers advice when necessary. No can do when you’ve crossed the line into sibling snogging. Your best friend doesn’t want to picture her brother in any type of sexual situation. If the hook up turns into something more, congratulations, but you’re still not going to be able to share certain details, because the guy won’t want you gossiping to his sister, and your friend won’t want to hear it. Dating the brother might also strain your friendship, depending on whether your friend resents your decision.
If things go sour with the brother and you remain friends with your BFF, you’re bound to run into him in the future. Another thing to keep in mind is that if things go sour, your friend will probably side with her bro, because blood is thicker than the those vodka tonics you guys share at the bar.
2. One of Your Brother’s Friends
Just like your BFF’s brother is off-limits, your brother’s friends are also risky business. Your brother certainly doesn’t want to imagine you hooking up any more than you do, and he certainly doesn’t want to hear any “locker room” talk among the boys once the rest of his crew finds out about your promiscuous ways.
3. A Co-Worker
Getting it on with someone from the office is up for debate. I have plenty of friends who have hooked up with, or are currently dating someone at work and have figured out a way to balance work and pleasure. Still, tread lightly. A one night stand with a co-worker can easily go awry, and you don’t want to zone out in a meeting because you’re recalling the multiple orgasms from last weekend. Also, if the rumor mill churns out a he-said/she-said account of the fling, you’re going to have to face your colleagues around the water cooler and wonder if they still think of you as a professional. If feeling uncomfortable isn’t enough to turn you off from hooking up, remember that many businesses frown upon inter-office relations, and you could be jeopardizing your job.
4. The Guy You Only Hooked Up With Because the Guy You Wanted Turned You Down
You get decked out for a party with one goal: Hook up with Joe. You get a decent buzz on and walk in on Joe making out with some girl on the sofa in the middle of the party. Feeling rejected, you engage in conversation with Tom, who is more than willing to swap spit with you. The next day, you regret Tom, and Joe changes his Facebook status to “In a Relationship.” Double burn.
If you don’t know the guy, aren’t attracted to him, or don’t have feelings for him at all, you are a thousand times more likely to regret adding his notch to your belt. It will also definitely add to the morning-after “What was I thinking?” factor.
5. Your Strictly Platonic Guy Friend (Until Last Night, That Is)
Can guys and girls be close on a strictly platonic level, or are feelings bound to be stirred up by one or both parties? Not only can hooking up with your best guy friend change your relationship forever, but it can also be disappointing.
Case in point: I was super close with a guy in college, and everyone thought we liked each other (we didn’t). The rumors alone weirded out my friend, because he wasn’t sure if he should believe them. We worked through it, and when he transferred, we kept in touch. One summer, I went to visit him, and it was like nothing had changed…until we had sloppy, drunken, mismatched sex later. I think it happened out of sheer curiosity, and we learned that our naked bodies simply don’t mesh well together.
We said our goodbyes the next day and pretended that it never happened. The end.
6. A Girl. But You’re Straight.
If you want to experiment, college is the perfect time and place. When I was in college, it was the norm to see girls making out at parties or bars, for no reason other than shock value and attention. Then Katy Perry’s runaway smash “I Kissed a Girl” came out and glamorized same sex experimentation.
There’s absolutely nothing wrong with same sex relationships, and nothing wrong with experimenting. But making out with your girlfriends can lead to just as excruciating an aftermath as a one-nighter with your guy friend.
Anybody out there have any experiences that fall into any of the above categories? We’d love to hear them, along with any other types of awkward sexual situations that we should all learn to avoid.
[Photo courtesy of thenoyes.com]



Stephanie says:
Tue, 23rd Sep 20087:19 pm
4. The Guy You Only Hooked Up With Because the Guy You Wanted Turned You Down
K, so I was at a wedding reception when the guy I wanted told me he wanted to get it on with *Dev* and was going out with her that night. I left the party, called up my Hook Up dude to get my mind off the guy I wanted.
It made me feel better. Haha
Erin says:
Tue, 23rd Sep 20088:37 pm
Your ex’s roommate.
What have I gotten myself into…
Laura says:
Tue, 23rd Sep 20089:59 pm
My best friend has a twin brother.
Lets just say. it’s been interesting
Capri Sun says:
Wed, 24th Sep 200810:03 am
Ex’s best friend! He’ll either think you were hooking up behind his back or you’ll be wondering if you secretly harbored an attraction to him the whole time you were with your ex. The truth is, being with him just reminds you of boyfriend and it’s kind of like a consolation prize.
unfortunately, he’s usually a really good kisser too…
Amber says:
Wed, 24th Sep 200810:55 am
I was mad at my boyfriend and so was his roommate, who was also a close friend of mine, so when my boyfriend and I broke up the roommate invited me over and we’d hook up just to piss him off then laugh when he left the room. I slept over once and he tried to go a little too far so I ended up losing my friend too.
And I was at a party one night where I hooked up with this guy that I thought was really cute, then he left and I was there with all the couples so I started hanging out with the only other single person who turned out to be the first guy’s roommate. I have some bad luck with roomies.
Kathryn S says:
Wed, 24th Sep 200811:20 pm
LMAO Amber. You win.
sara says:
Thu, 25th Sep 200812:28 am
#4 and #5 should most definitely be avoided. However I’m in debates about #3 because after months of hooking up with my boss (oops) we are in a great relationship. I guess it depends if its a one-night-stand kinda hook-up or more like a little dating-but-not deal.
Jenny-WMU says:
Tue, 30th Sep 20089:50 am
Capri Sun – omg, I’ve been so there! LOL
Elizabeth says:
Tue, 30th Sep 20087:36 pm
Ex-boyfriend/former roommate’s close friend/current roommate.
It’s pretty complicated and happened..oh two days ago.
I need to meet someone outside of my address.
Lauren says:
Tue, 14th Oct 200810:57 am
#2 A drunken one night stand and this is bad. . . not only is he my brother’s BFF, he’s also his roommate. My bro and I are real close, I’m probably over there 2-3 times a week. AWKWARD! Oh, btw, my brother laughed his ass off and smacked his roomie in the face. But it’s all good, we’re all friends now, hung out yesterday as a matter of fact.
sunshine says:
Wed, 15th Oct 20082:44 am
how about dating your ex boyfriend’s brother’s best friend.
lets just say i lost 2 friendships.. my ex’s brother and his best friend… it sucks! and i didnt do it to get revenge i just was really attracted to him…
and havent spoken to either in over a year and now the ex wants to be friends after almost 3 years and i want nothing to do with him but i want my friends back
Becca says:
Wed, 10th Dec 20082:05 am
how about your roommate…. during your first semester…
… I love my life…
odd says:
Mon, 22nd Dec 200812:47 am
Ive got one that’s worse than all of these: drunken one night stand with stepbrother … lets just say that family get-togethers have become incredibly AWKWARD.
Dave says:
Wed, 24th Dec 20085:26 am
odd… lolol.. man. what a situation.
Mike @ PSU says:
Thu, 25th Dec 20086:25 pm
Laura, I’m currently going out with my friends twin sister. It’s a little wierd sometimes.
snwbrdrgirl says:
Sun, 1st Feb 200911:56 pm
#3 – definitely a good situation to avoid – way way too awkward as I have discovered twice now :0
#6 – lol. I was at a frat one night with a couple friends, and I don’t remember this very well, but apparently a girlfriend and i bet two guys that if they would kiss, we would make out…well apparently we did and it was videotaped…ya it’s prob on the internet somewhere, though i have never seen it, but prob not my best decision making moment lol
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