So I like this guy... (Isn't that the way it always starts?)

So I dated a guy I'd just met casually for a couple months, about half a year ago. Then he went on two dates with someone else he "really liked" who was friends with some of his friends, and so broke it off with me. Part of me guessed that meant that he wasn't really that attracted to me, although I'd been acting fairly distant and casual so there was some ambiguity, I think, as to whether he thought I was only looking for something casual and he wanted a relationship with someone... He was also on the rebound (well, so he said, he'd actually been single for almost a year at that point) from an ex who he'd been good friends with, who was smokin' hot, and with whom he'd had a bad and unexpected breakup.

We hung out a couple more times as "just friends," then I left to go back to school and he asked if we could stay in touch, and said he was really glad he got to know me and stuff. And we've stayed in touch, because we have pretty fun conversations every couple weeks or so, and at times in our conversations he keeps insinuating that he thinks I'm an especially attractive person (volunteering that opinion, not that I'm fishing for compliments). And the woman he was dating when I left, well, she is listed as "single" on her online profile -I don't know whether they're still dating, but I'd guess it hasn't yet progressed into a serious relationship at the least.

And School is over in like another month, and I think I should talk to him about more "our situation", because the only conversation like that we ever had was just a few minutes long and kind of vague, when he was telling me he'd met someone else, and I guess he must not be aware of it, but when he compliments me now it twists me up inside and I don't know how to deal... And I'm sure he expects me to at least hang out with him some -I've been kind of friendly to him because I can't help it, but also I don't want to drive myself nuts being so confused...

I know I can't know exactly what is going through his head. You guys can't either, really. But any ideas as to some different possibilities? Or how I could have a conversation with him about what is going on?

I'm not saying I want a serious relationship with him -that would make no sense. But whatever happens between us I just really need to know that he wasn't faking things when we were dating, and that he's not condescending to me or "just trying to make me feel good" now when he compliments me...

I'm not sure if I completely understood your post or not, (my eyes are too tired to read it again) but Im just going to answer with what understanding I have...

Seems like this guy is leading you on.. I liked a guy that I used to work with that did the same type of things, he would give me complements and text me things like " let's make love" (when he was drunk) and just give me a lot of attentsion and so I would try to hang out with him outside of work because I thought was liked me too, but he would always flake and make up excuses and then he would tell me about the girls he was hooking up with, and it was so confusing to me.. I think he would flirt with me to tell me I was pretty so I would feel good and then develop a crush on him and that would in turn make himself feel good, he was totally leading me on, just so he can say that all the girls at work like him, and that he's a pimp..

Don't waste your time with this guy, he seems like a jerk that's playing with your emotions and you deserve better!

This guy is not a bragger -he's not very stereotypically "manly" really, more of an artsy type. We have serious conversations about other topics -it's not like the only interaction we have is flirting or something... That's not saying it couldn't be partially an ego thing -of /course/ that's a possibility...

And okay, I know this is kind of dumb, but I get like a 7 or 8 on most of my pics at "hotornot.com"... so I think I'm decent looking, and I think it's possible he's attracted, or has gotten more so as he's gotten to know me.

But again, I'm not looking for assumptions here one way or the other (especially since me and him are very unusual people in a lot of ways anyway) -I'm looking for ideas of ways to communicate to him and sort this out...

Don't assume that a bad breakup can't keep a guy off balance for more than a year. Been there myself. Took over a year after my first big love to have half a clue and I had a rebound along the way... not intending to... was just too stubborn and lonely to not try to shake the previous girl off with a new relationship. Took a shot. Ended up hurting another girl. Guilt on top of idiocy.

Uhm... what to do? Hold back, be nice, and be careful. He might be a great guy who just hasn't found his footing. He might be a manipulator who senses you are interested. I don't know.

But I think you like him a little too much for comfort, right?

So since you don't know his intentions, you need him to do the work. He needs to chase you. You can be kind. You can be nice. But he needs to be willing to do the work to catch you.

The only problem is... some guys just want to do the work to get the catch. And then no work after. The honest truth is only time will show if he is for real but just unsure... or if he's just a guy who likes to play around and see who he can hook.

My advice? Don't wait. Look around. See other guys. You aren't dating exclusively. If he thinks its too much work to "win" your attention... then he isn't really worth the wait, right?

"you arent dating exclusively."
We're not dating at all, as far as I know.

I wouldn't really say I'm waiting around for him. I'm just in an awkard transitional phase myself, since school is over in a month so there's not much point in trying to start something here, even if I /could/ meet someone...

It's more just that, I feel like to hang out with this guy even as just friends this summer and enjoy myslef, I /need/ to know what's going on. I need to be able to trust him.

It's like how I have a guy friend I've known for years who I know likes me, and who I know I don't want a relationship with -I don't know if it hurts him but the whole thing is very comfortable for /me/ because I feel like I /know/ where both of us is at. With my old friend we went through periods where he didn't like me, and now he likes me, but not, I think, a crazy amount. He would hook up with me if I wanted, but more than anything what we have is a bond built up over years of friendship. And we can talk about almost anything, and know lots about each other's romantic lives. Picture Harry Met Sally, seriously.

And with this other guy I actually dated, for some reason it's like we talk with so much comfort and about so many topics, almost like old friends, and we just fall into that pattern naturally, but the difference is I don't know if I can trust him that well, even though it's tempting to do so... I don't know, it's screwy. I haven't experienced a situation like this before. So if I go back this summer, and this guy wants to hang with me, I need to be able to trust him more in order to form a more genuine bond, I think, and to stop hurting -or else I feel like I'm almost being deceitful to him, like our friendship is a charade on /my/ part. I guess it's my belief that genuine friendships can weather crush/lust drama bull... but I'm an idealist.