Long story short, we met 2 years ago and we're really really close. This isn't your normal 'friend-turned-crush' issue because I liked him that way right from the beginning. I never told him, but at one point it kind of got out through my other friends. I managed to execute some damage control by making it out to be just a huge prank/joke. Something tells me he never quite fell for it though. Either way, he never responded in any way.

Fast forward to recent times. Last Monday, we were working on a school project after school in a nearby café. I skipped school that day, so I just met him there later. Bearing in mind that this was right after school, and the café is just opposite my school, I was quite surprised to find that he'd actually taken time to change out of his uniform into... how shall I put it? Something dressier than what he used to wear even when he went out for dates with his ex.

Second surprise: Now, both of us are quite comfortable with physical contact between friends so this isn't as big a giveaway as it sounds. But I think bare skin against bare skin is a bit much, yeah? Especially when said skin belongs to my leg and his. Not that I'm complaining. (Cough) AND this actually happened several times throughout our 'project-date' for up to about 5 minutes each time. I swear that I wasn't the one who initiated the contact. Also, since this café has sofas instead of chairs and we were sitting side by side, it actually got to a point where we were basically leaning against each other. Again, for quite a prolonged period.

Third surprise: He wanted to pick up the tab. (Yeah, we had our lunch there) To the best of my knowledge, he never does that with his other friends. Ever. Even if they ARE girls. Of course, I didn't let him pay. That would be dangerously like a real date now, wouldn't it?

Fourth surprise: That night, when we were chatting over the phone, the topic of relationships cropped up. (Yes, we're in that kind of friendship that we can talk about anything without it meaning anything extra. And yes, he calls me a lot. But always with a valid reason-homework, exams, etc.-even though we usually sidetrack from the main reason he called) So, somewhere near the beginning of our friendship, this same issue cropped out where we were talking about our ideal partners. His was the typical 'sweet, traditional, kind, blablabla-you know the drill' kind. Me and my friends threw books at him for being so stereotypical. :rolleyes: But anyway, my point is, that night when we were talking about the same issue, his ideal partner was no longer that. In fact, he said "I've basically given up on those types. I don't think they would suit me after all. Someone edgier, more interesting, with more substance and says things like 'I will kill you' instead of 'my dear dear boyfriend' would be much better. Someone fun to be with." I almost started hyperventilating then. Not to be narcissistic, but he'd just described me. He'd used almost exactly the same words I'd used in a post on my blog describing myself(And yes, he read that post). In fact, the words 'I will kill you painfully' had just been uttered by me that afternoon.

Well. That's basically it.
Only... I don't know why he does this, but he flirts with my best(girl) friend. Nothing over the top, but he does say things like "I miss so-and-so" whenever she doesn't come to school or plays with her hair and stuff. Thing is, she's his close friend too, so it's hard to judge what he's really up to. Comparing me and her though, he definitely spends much, much more time with me. In fact, he once told me that he's pretty sure I'm the only one out of his group of friends that he'll keep in touch with after high school. And before you point out that he could be saying that because he was talking to ME at that time, he's not that kind of person. He's more of the I-don't-like-you-so-Imma-tell-it-to-your-face variety.

So. I'm done now. What do you think? He likey? He no likey?

I'd say he likey and that you should ask him point blank. What do you have to lose? Put it out on the table and let him know how you have felt the last couple of years as well. You could tell him you never brought it up before because you didn't want it to effect the friendship if he didn't feel the same way, but you have been getting some pretty strong signals that his feelings may have shifted.

It sounds like you have the sort of friendship where you could be that open and honest without fear of it ruining the friendship if it turned out he wasn't thinking that way. You would both just have a good laugh about it.

It may turn out you have a great foundation for a "more than friends" relationship. If you did go out, and it was just too weird to be "dating", if nothing else you would still have that friendship.

Instead of presuming and assuming, just tell him you think he would be a great date and ask him out and see what he says. You have been talking around each other long enough, so talk to each other for a change.

Thanks, Doula and talaniman for the advice. Much appreciated. :)

Bring it up.if he says he doesn't. Just laugh it off as a prank.