anella, 17, from california, asks:

So there's a guy at school who I've known for a few years now, we've always been friendly but never great friends. I never had any interest in him until earlier this year. Honestly I don't even know what it is about him that I like so much.. he's not bad looking, but definitely not gorgeous, and he's shy and a little bit socially awkward. Our junior prom was a few weeks ago, and neither of us had a date, so I decided to casually ask him if he would like to go with me. He said yes, seemed happy about it, and we had a good time, despite how nervous he was. For a few days after we talked a lot, but then he started backing off, and the past week or so we have barely talked at all. Mutual friends say that he likes me, and I really wish we could hang out outside of school more, but I don't know if I should make a move. I know he's shy, but I already asked him to prom, shouldn't that give him enough confidence to be friendlier with me?

VictorM's advice:

No. Shyness is not about confidence; it's about trust. He doesn't trust you enough yet to not say "no" to him, so he doesn't ask. Not going out with you is better than you saying "no" to him. That's what he thinks (subconsciously anyway).

You may have to take the initiative a few more times, and be a little patience until he breaks through the trust issue. With some shy people it takes longer than others, but once the barrier comes down, he'll be fine. Most shy people drastically change their behavior once they trust a person.

You can make it easier for him to ask you out. For example, if he talks about wanting to see the new Pirates of the Caribbean movie, say to him that you too would love to see it so when he goes to ask you to go with him. You need to be this direct; hints don't work too well.