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."
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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.1