Go for it! Guys like a girl who has confidence, and it certainly takes guts to ask someone out — now you know what guys go through, eh? Plus, if he's really that shy, he might be relieved at your asking. It takes the pressure off of him.
There is a new guy at my school and I think he's cute, funny, and sweet, but he's really shy. I want to ask him on a date, but I'm not sure if I should, and if I should, how?
Before you ask him out, take a few days to gauge his interest in you.
Hang out with him just a little bit more than usual. Try to walk with him between class periods or talk to him before class starts.
Have good eye contact. Aim for the middle ground — too little eye contact and you'll look uninterested or too shy, yourself; but too much and you'll intimidate him, or just come off as creepy.
Laugh at his jokes. You say he's funny, right?
Smile at him. Look over at him once or twice during class or at lunch and flash a pleasant smile — again, nothing too big (you're not a beauty-pageant contestant), but nothing so small that he might not realize that you're smiling at him, either.
When the moment comes to ask him out, be direct. Say something like
- Would you like to hang out at the mall on Friday?
- I'd love to see this new movie; would you like to come with me?
- I heard about a new Greek restaurant; want to try it with me?
The worst he can say is no, which is a little embarrassing, but then you know where you stand. You can move on to greener pastures in the romantic field and start turning your crush into a friendship. (Just because he doesn't want to date doesn't mean he wouldn't make a good study partner.)
When you're on your date, you might offer to pick up the check. Doing so will avoid any confusion about whether the two of you are on a date or just going out as friends. Let him know that if he wants to, he can pay next time. This puts the ball in his court, if he's interested. Whatever you do, don't expect the boy to pay for both of you when going out was your idea.