Shy and inexperienced... Advice?

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Clocky

Last year, I was in a class with this guy I like. He was rather geeky,but I am kinda geeky too. He sat behind me, and we usually talked, when we weren't listening to the teacher lecture. I suck at flirting, so I just tried to be myself and laugh at his jokes and stuff. I don't really know if he liked me. He would often show me cool graphic artists that he thought were like my drawing style, which I found interesting. We sometimes compared iPhone apps (did I say geeky enough for you?) and talked about photoshop. (He knew a lot more about it than I did, but I still liked talking to him.) We had this thing where sometimes, fairly often, one of us would see the other in the hallway and say the other's name really fast, and we would respond with their name. He even came up to me and my friends once to take pictures of us for his photography portfolio. I think we had a decent amount in common, even though I didn't get to know him super well. However, I was really shy to ask him out or anything (I've never had a boyfriend because of it) and nothing came of it that year. He has a really tight, big group of friends (which I sorta know because all of them were on my co-ed soccer team, including him) but I couldn't really hang out with them, because their group is sort of impenetrable.

Anyway, I still liked him when school started after school, even though I hadn't seen him at all. And now, I don't have any classes with him. I was planning to sign up for co-ed soccer again this fall, but I signed up too late and they didn't have space. I don't even hardly see him in the halls either, because our classes clearly are in different parts of the school. I try to smile at him whenever I see him and do the say-the-name thing, but often I chicken out and pretend to shuffle through my bag. I still don't know if he likes me (He has a lot of friends, and seems like a friendly guy to everyone) and it's likely he has probably forgotten me.

My question is, do you think I should just try to forget about him? I have been thinking about him a lot lately. I'm VERY picky about boys, and I could sort of imagine actually being in a relationship with him - but at the same time, I'm so inexperienced that I'd probably embarrass myself no matter what I did.
Do you think I should just drop it and move on? How could I potentially get to know him? I know people would say "Just go up to him and start talking!" but I don't have him in any of my classes, and he's always hanging out with his supertight friends. I just don't know... I'm such a loser when it comes to boys, and I feel so weird about it. I know you are probably reading this and just seeing a confused, lame girl who has no spine, but I just want to find someone who likes me and who I like and see what happens.

Answer
Something like this happened to me last year, so I understand how it feels to want to get to know someone better (and possibly have a relationship) even when it seems like everything is against your favor...

When you see him in the hallways, be friendly and approachable. If your ignoring him, then he'll probably get the impression that you don't want to be around him. Just look him in the eyes and flash a genuine smile. It sucks that your class schedules are so different, but maybe you could connect with him on facebook or IM him on Gmail or AIM, yeah?

Good luck!

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Title Post: Shy and inexperienced... Advice?
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