Should I risk it?

[janesmith]

I'm a freshman this year and I don't have too many upperclassmen friends. I met this one guy (a junior) through a band/orchestra activity we both joined. I see him around school sometimes and when we're not in a hurry we always stop and talk. He's usually the one saying "hi" to me but I always greet him too. When we first met, he was extremely nice to me and would always help me out when I was packing up my stuff after practice. We have long facebook chats about music and bands and stuff like that. We say stuff like "you're my best friend" or "i'll love you forever" and things like that. So even though I've only known him about 2-3 months I guess I can say we're friends.

 

So I kind of like this guy. I don't know if he likes me back. I don't obsess over him or anything, but I wouldn't mind going out with him sometime. The thing is I have virtually no experience with guys. I used to live in a different country and i was a stereotypical "good girl" (never skipped church, perfect grades, didn't spend much time thinking about guys). I also was EXTREMELY slack about my personal appearance. I mean we did have uniforms (bleh) at my school, but I didn't really make any effort to look "attractive" to guys. Now that I moved to America, I'm a lot more comfortable with the whole 'casual dating" idea and I definitely present/carry myself better than I used to. The problem is that my lack of "experience" is kind of affecting my interactions with guys now. I have been asked out several times, but I've always turned them down. Now I have no idea how to get this new guy to "like" me or how I should imply that we should go out. I don't want him to think I'm one of those clingy obsessive girls, because i"m not. I also don't want to ruin our friendship and make things awkward. If he ends up liking another girl, I won't cry over it but I'd much rather he like me

 

We don't have any mutual friends because we're in different grades, so I can't really get my friends to ask him if he likes me. He's one of those guys that girls obsess over in like a "cute older brother" way but from what i know, he hasn't had too much luck in the dating department either.

 

Some of my friends want me to go out with an older guy because I'm pretty mature for my age (mature meaning I prefer a stable relationship to hooking up) but at the same time, this guy is graduating in less than two years.

 

Sorry for all this writing but I kind of felt the need to explain my situation. So any advice on what to do? Should i risk him finding me a complete weirdo and screwing up our friendship, confess to him, or just let him go?

[MikNomis]

Risk it I say, by the sound of it even if he weren't interested in that way towards you, your friendship will remain.