Ask A Guy: How To Tell A Casual Hookup You Want To Hang Out Again

Hi Joel,

A couple of days ago, I fooled around with a guy, and now I really feel like texting him. We were drunk and don’t know each other very well, he is a friend of my sister. I know that it was a “just-for-fun” thing for him, but I want to change that, and I want to see him again. The most important question I have is what should should I text him if I text him at all?

Whether it was just a drunken make-out session or an all-the-way one night stand, post-hookup conversation with randoms can be one of the most difficult things to navigate, but in your case it should be a bit easier since you know him through your sister.

Before we get to the “what do I say,” one word of caution: if this is a good friend of your sister, she may not be too cool with you going after him. Dating friends of the family can be weird to begin with, and when it’s between siblings, doubly so. My first piece of advice is to mention it to your sister, and if she’s cool with it, go right ahead. If she has a big problem with it, I’d rethink things as it may not be worth the drama. But if she’s ok with it or if he is just a casual friend, there shouldn’t be a problem, but it’s best to play it safe from the family side.

Moving on to the actual guy in question, I don’t think there’s anything wrong with shooting him a text to see if he wants to grab coffee or get together in some other relaxed “we had fun, we should hang out again” sort of way. Just keep it really simple and test the waters. If you know something the two of you have in common, build off of that as it will make the initial conversation easier. Don’t come on too strong because that could come off as overly needy or something along those lines; but at the same time, don’t be afraid to let him know you’d like to get to know him better.

BUT, know that there may be an expectation on his end of hooking up again, since that happened already. I wouldn’t come right out and say “we’re not gonna hook up,” but just be aware that it could be something he’s expecting to happen. Make plans for something during the afternoon or weekend day, as that will help keep those ideas mostly off the table.

Bottom line is, if you don’t ask, you don’t get. So give him a shout and hopefully you’ll find yourself at the beginning of a new, great relationship.

Best of luck!

Joel Freimark has done a lot in life and seen even more. From last minute international travel to bizarre places to writing award winning books, he’s here to bring his wisdom to all your problems. He hosts a weekly advice series on Youtube and a music series also on YouTube.. No question is too outrageous or personal, so go ahead and fire away! Follow him on Twitter.



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