Guys are so confusing. Help?

Question

Okayyy...here are the facts:
I'm in highschool, I met this guy that's a couple years older than me, about a year ago (he's in highschool too).
We've hung out in the same group a couple times. The first time we went skiing and he helped me out the whole day 8). He's very gentlemen-like (holds doors open, etc).
I'm not cocky in the least, but have told that I'm extremely attractice, and am hit on by guys all the time...Although, I am UBER conservative, and have never even held hands with a guy before. The guy I'm talking about I like ALOT...he's kind of quiet, and from what I hear doesn't have much luck with girls. We talk on-line occasionally (intiated by him alot of the time)...He commented a picture of mine on-line saying that I was "beautiful".

BUTTTT, when I see him at school (which is rarely) it's super hard to tell if he's interested...He's really quiet, and I have to do the initiating in person. If he liked me back, wouldn't he put forth more effort?

Answer 1

Not necessarily. A lot of guys that age are lacking in self-confidence and are so intimidated by pretty girls that they get tongue-tied around them. That would explain why he IM's you, but doesn't talk to you very much in person. Give him a chance if you really like him. Assume that he won't have much to say to you before you approach him, and have some things in mind to ask him -- open-ended questions that he'll have to respond to with more than a yes or no. Assuming he likes you -- really, why wouldn't he? -- he'll get over his shyness or nervousness around you as he gets more comfortable being with you, and your relationship will blossom. Even if for some strange reason he doesn't like you "that way," you'll have made a good friend.

Answer 2

Some guys are really quiet and shy, and self-conscious around girls. Why not ask him to help you study for a test, or go for a bike ride, or just go hang out at the mall? If you both seem to hit it off, it might be time to try to hold hands. After that - well, take it slow. You both sound young, and there's no need to rush things.

If you're nervous about doing this, think of it this way: What's the worst that can happen? He's a gentleman, so at worst he'd say thank you, but he can't make it that day. The upside is that you might really hit it off, and maybe start dating.