Should I just stick it out or run?

This is going to be long. I'm really, really sorry in advance. :P

I've never really been much into the dating thing- Some flirting here or there, but I have always been too busy for it to be anything serious. I'm 17, and kinda-dating a friend of mine- I'm just really unsure if I should give him a chance, a real one, or just drop it.

I've known him since middle school, and he's dated basically everyone in our group and then some. He's in my grade and actually pretty nice- Which, I hate to admit it, is really good for him. He's smart but doesn't really apply himself, can be a little melodramatic and woe-is-me-ish, and has a terrible reputation. Not for like crime or anything like that (I go to a "small town" school of 1800- A bad rap for crime would be like destruction of school property or something lol. Just for personality and dating- He can be a tad clingy, and is in general known for being weird, except to his friends. He's not popular, not really- I mean, within the circles he travels he is, but those circles are lower on the food chain. I guess he's just not....stable. He's not terrible looking, but he's not drop-dead gorgeous. http://sphotos.ak.fbcdn.net/hphotos-ak-snc4/hs002.... Dating or otherwise associating with him on a relationship level has a terrible social kickback- The teasing is bordering on merciless. Hell, I've participated in it.

But I went as his date to Homecoming, as a friend thing, and we kinda hit it off. We had fun and I probably let him get away with/ encouraged more than I should have. I do like him and would like to give it a chance, but I'm fighting with myself.

He's asked me out, although not in so many words. He was going to do it on Wed, I guess, but I "guessed" it earlier.

I said we'll see where it goes, and I'm trying. It's just that I guess I'm second guessing myself- I say that I like him, and at the same time I think of all the things wrong. I say I had fun, and at the same time I'm wondering what others thought. I hang out with him in the morning and am really jittery because I'm worried about what others will think and say. I know I shouldn't- And I'm honestly considering pushing on with it just to get over myself- but I do. I'm just not quite self-confident enough, I suppose.

I mean, he's had some mess ups- His status after the dance made it sound like we were doing a LOT more than we were, and he tagged me in it. We're going to the movies tomorrow and he felt the need to tell everyone in his 3rd block class. I told him to keep his mouth shut (Except nicer than that, lol) and that helps, but I guess I worry most about when we break up. He's very into this, and we are not even officially dating- I think getting rejected a lot has made him a little overzealous. He's been getting up an hour and a half earlier than usual so he can meet me at school (I get there very early), insisted on buying my ticket for the movie, and is 99.9% going to give me some sort of jewelry. (I don't really care for gifts, they just make me uncomfortable) I'm just worried that he thinks of this as being more than it is, and that it'll really hurt when it crumbles. I'm willing to give it a chance, really- I am. I want to. But realistically I'm doing this for fun, not because I think I could marry him. I want to tell him to back off a tad, but I don't want to turn him off or hurt his feelings.

So what do you guys think?