*Smile
*Always be attentive when he talks
*Think of reasons to be near him (like you said he was a skater - try to frequent where he hangs out) or go to where we works
*Pay extra attention to your looks (such as fixing your hair pretty, wearing nice clothes)
-I suggest you doing something to make yourself feel pretty - like getting a manicure or pedicure, buying a new top, or maybe even get your hair fixed. Guys like it when a girl is confident. If he likes you - he'll come around.
-You could also do what I did when I met my husband....I was 19 - he was 18. He worked at the local gas station at the full service (where he pumped the gas for you). Anyway - I went and got gas everyday for a week. I would say to him to fill it up - and it would only cost like $1.50

HE STILL DIDN'T GET MY HINTS! I finally told him after I had went everyday for a week - that I thought he should call me - and gave him my phone number. And we have been together for 9 years now!
So - if you think he is just really shy & you are really into him. And of course if he doesn't catch your hints. I think you should go up to him - be blunt - and tell him that you've been thinking of wanting to go out or you were thinking of wanting him to call you
Good Luck!