How do I pursue a Hook Up without looking Crazy?

It's not like we've only been hook ups. We started as friends and it took us forever to finally gain the courage to start hooking up. I sleep over and I've talked with his parents in the morning (they were over a couple times when we woke up) and I'm even good friends with his brother. He isn't very good at expressing how he feels, but I do know he likes me. How do I pursue it without looking crazy? If it took us this long to get to this point, I don't want it to take equally as long to pursue things, but I also want him to know I care without straight up being like "Hey I have feelings for you, I care for you."


Most Helpful Guy

  • You're not pursuing a hook-up. You've already started hooking up... talking to his parents in the morning... good friends with his brother. You guys are seeing each other. You are what you Do -- not what you label it. Now, official "terms" is awkward. You don't have to go that route, but just recognize Reality -- you're seeing each other. But yeah, when you start off as friends, and things just sort of 'happen' over time -- you want to let him know you really care about him without scaring him away or making things weird, right?

    Well, good news is, it's already at a point where it's not weird. You just say it as if you're talking about a good movie you just saw. No huge conversation required. You're just throwing it out there, as if it's already kind of a given anyway. :)

    "You know what, Brian? I'm glad we're more than just friends and we've been seeing each other some. I have real feelings for ya -- that's cool, right? (wink / smile)." Get his feedback. Again, this isn't a serious tone, it's a happy tone -- like noting "Yeah, I'm glad we saw that movie, I really liked it -- I'm glad we went and saw it."

    Again, you're not saying this after you guys first hooked up. Things have already established themselves somewhat -- and you're just pointing out the obvious. Your tone/attitude of having a cool/fun demeanor about it is Key. It avoids making anything a big deal, and allows him to open up and give his 2 cents in as well.

    • Haha oop, thank you for catching the little grammar error there! Wow, this was extremely helpful, thank you for opening my eyes in a way!


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What Guys Said 2

  • The best way to tell him is by letting him know for god's sake! Jesus woman, stop asking rhetorical questions! Lol

    P. S. You will NOT look crazy unless you give him weird faces while jumping around him and beg for his expression of feelings towards you. ha ha :P

    • Ok, so you're a guy (obviously haha) and just to be clear, it WON'T scare him off if I subtly bring it up? I think that's why I'm so reluctant tbh

    • Show All
    • This actually really helped! Wow thank you! Wish me luck! haha

  • So your having sex and you think saying "Hey I have feelings for you, I care for you." is crazy?


What Girls Said 1

  • Guys don't like head games, be brutally honest with him. You don't need to waste your time if you're looking for a true commitment and he's not. Both of you need to be on the same page unless your ok with just being his fuck buddy. Tell him straight up and see how it goes, only way to do it!