Mixed Signals from my best friend...who I'm in love with

I should really be sleeping but I would rather not sleep than deal with this alone.

To start out, I'm gay and 20. One of my best friends who recently came out to me and everyone else is 19. I really value our friendship and he has always been there for me no matter what.

Over the summer we became much closer than ever before. In July this year I began to fall in love with him. He always seemed to show a lot of interest in being around me but I assume that it may be because he didn't get a chance to be around any other gay guys before that. He now attends the same university I do...

To keep it short, he's recently been sending me really mixed signals. One night I was sitting next to my bed and he randomly started to give me a head rub. Later we were laying on my bed talking to 2 of our friends and he was basically spooning me and had his arm around me, and I put mine around him. This made me think that there was maybe a possibility that he liked me.

Since that moment a few weeks ago, whenever we're laying next to each other it ends up with us just cuddling and listening to music or something. We've never acted in this manner before. We always have deep conversations but we've had a few cuddling sessions where it seems like his voice is just softer and that he's really trying to open himself up to me. I'll have my face directly up to his and I can rub his hair and ear pretty romantically without him moving away, and he's done similar to me. One time he even spent the night in my bed and we were essentially cuddling in just our boxers (kind of weird for just "friends") and he let me lay on his chest till I fell asleep. He even holds and strokes my hand when we're cuddling like this. My friends all comment on it and think it's strange. He also recently started wearing things I like and gets obsessed with the music I listen to.

However, he talks about other guys ALL the time. He's never really been with a guy and I know he wants to "experiment" and such but he's always mentioning which guys at our school are hot and says that he would get with them. Occasionally I'll mention a guy that is interested in me and tell him that I don't feel the same way, and he tells me that I should go for it anyways and if not then to introduce them to him. It really hurts my feelings that he does this because it messes with my mind horribly. I try to stop liking him but then wonder if it's a bad idea because I truly feel that we could be together and I know I could make him happy. He once said to me that he felt like he could be a good boyfriend (not MY boyfriend specifically) and that he wouldn't be opposed to a boyfriend. Whenever he talks about guys I just have no idea what to do and I kind of stop talking because he's the only guy I'm thinking of. However we are at different stages of our lives and I have been open about my sexuality for 2 years and have had plenty of time to experiment while he hasn't. It's horrible because I get mad at him and can be really rude if he talks about other guys when really I'm just jealous and sad.

So basically I am asking what you guys think because I have no idea. I'm really afraid to tell him I have feelings for him because we've been friends for over 2 years. During summer (about a month before I began to have feelings for him) we drunkenly hooked up because I blacked out, and I made it clear that I didn't want it to happen again, but our relationship stayed the same. I also found out he told my friend at the time that "it would never happen again." It's weird that I started to like him after the drunken hookup.

It's driving me insane and I'd really like to know what you guys think. He's not the type of guy to play stupid games like this and I'm really hurt by it. Any input would be great.

Thanks.

He isn't playing any games. He just doesn't know what he wants or how to act. If you like him, just tell him. Tell him you would like to go out with him. If he isn't interested, then you will know. Will it hurt the friendship? Maybe, but only if you two let it. But the ways things are now are not helping your friendship any. Just try to be open and sensitive to how he may be feeling. Like you said, you have been out and dealing with things longer than he has, so think about how he may be feeling.

Good luck.