OK, here's the full maybe not so complicated story:
I just recently "re-met" a friend of mine. We'd hung out once or twice a couple of years ago after meeting in a chat room and realizing we went to the same high school and he knew my younger brother. Anyway, just a couple of months ago we started hanging out again since my school-life got a bit less busy than usual, and the past month or two we've seen each other like every weekend, though we are not officially dating.
I have no idea how much to emotionally invest in this. Sometimes we're all cuddly the whole time, other times it's just a kiss and hug when we meet and then a kiss and a hug when we part. Over the past two months we've had sex twice and it is the most amazing sex I have EVER had in my life. It's not that shitty "trick" sex, but that passionate, pass-out halfway through sex with alot of feeling and major making-out going on during the act.
This doesn't feel like infatuation, because I've had plenty of that. I have this kind of deep caring for him that I've only had with maybe two other people that eventually had to move out of my life, and the only thing I think about it everyday is when I'll see him again.
I know I should probably just bring it up and ask him out on a real date, but some other friends of mine think he might like the kind of easy, no pressure, friendship kind of thing we have going on. I'm just horrid at reading people and would hate to make the whole situation highly uncomfortable. Should I just stop being a pussy and actually ask him out on a real date?
