13 Awkward Things That Happen When You’ve Been Hooking Up With Someone For A Long Time

Have you ever had an experience that just…changes you? And not for the better, either–for the much, much worse. I ask only because I have. It was at a recent Thanksgiving dinner during which my grandma’s boyfriend leaned over the dinner table to ask me, in front of the rest of the family, to explain youth hookup culture to him. This stuck with me because it was horrible, obviously, and I wanted to bludgeon myself with the turkey, but that’s not the point. I will #neverforget this moment, you see, for that I finally accepted what trend pieces in The New York Times and Salon had been telling me for a while–hookup culture, the one that millennials built and Generation Z has now accepted the burden of taking over, might actually be a problem.

While there’s much to be said in favor of casual hookups in general–they’re fun, easy, low-commitment–they can start to fray around the edges at a certain point. One example of this is, obviously, those occasions when you are essentially asked to explain your sex life to a senior citizen. Another is when you’ve been casually hooking up with someone for an extended amount of time. Has this ever happened to you? If it has, you’ll know that it can get a little…problematic. Among other things. Check out these awkward things that happen when you’ve been hooking up with someone for a long time:

1. There’s a certain point when you realize that, no matter how casually things started, it’s not super casual now.


It’s usually at the exact same time that you realize that you realize, oh, I’ve been hooking up with this person for a few months now. Huh.


2. But it’s not, like, serious either. 


It’s just….there.


3. You’re not sure whether it’s appropriate or not to ask them to parties or events with your other friends.


Even if you don’t mean it as a “thing,” they might take it as a thing, and then you’re both freaking about this non-thing thing that shouldn’t even be a problem in the first place, because it’s literally just your friend Emily’s birthday party.


4. So, you’ve devised a foolproof method for such instances–you ask them via text, but at the very last minute, making it very clear that they can come, but you “don’t really care” and it’s only if they have “nothing better going on.”


And it’s “no big deal” if they can’t.


5. Your friends always ask you what the deal is with you and “that guy” or “that girl.”


Like, all the time.


6.  If they’re not asking you what’s going on, they’re asking if you’re trying to date them “for real. 


Or “get exclusive.”


7. And, honestly? You’re not totally sure that you would.


You like hooking up with them, but dating is…a lot.


8. You also wouldn’t not. It’s just that you don’t want to, like, right in this moment.


That’s reasonable, right?


9. At the same time, you often find yourself going on weird, creepy binges on their social media pages to see if they’re talking to other girls. 


Like, FBI-level stalking.


10. You never feel good after you do it, but it must be done. 


That page on Instagram that lets you see what the people you follow are doing all the time was invented for a reason, after all.


11. Not that you care. You’re not actually dating them, anyway. Because you are “chill.”



12. “You aren’t dating them” and “stay chill” is essentially your mantra, actually. You are a chill, cool girl who goes with the flow.


You and Amy Dunne are similar in that way.


13. Every so often you get the urge to ask them, “Hey, so, what the heck are we?” but you resist.


It’s not that you’re scared of the answer–it’s that they might ask you what you think you guys should be. And what are you supposed to say to that?

Have you ever hooked up with someone for an extended period of time? What did you relate to the most on this list? Let us know in the comments!

You can reach the author, Sara Hendricks, on Twitter and Instagram.


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