One day while I was in class this boy that I have been flirting with told me that he liked me. That same day he asked to kiss me, but I told him no. He has been asking me for a kiss for the past 5 weeks now, but he doesn't officially ask me out - he just says "If I asked you right now to go out with me, what would you say?" so of course I play hard to get and say "maybe."

I really do like him, but he is always flirting with other girls. Plus he has a girlfriend on top of that. So what should I do - should I kiss him, or what?

Hopefully you can help
From,
The troubled school girl.

Dear TSG,

This guy sounds like trouble. He wants to keep his options open - flirting with lots of girls, even when he has a girlfriend.

If their relationship is definitely over, and you're really interested in him, the best way to deal with a guy like this is to try to pin him down. Next time he comes to you with a hypothetical - If I asked you out right now - respond playfully with, "Are you asking me out right now?" A yes or no question will force him to come out and say exactly what his intentions are instead of stringing you along.

Take care,
Jonathan

I'm a straight guy but everyone thinks that I'm gay because I hang out with girls a lot, watch shows like The O.C., and dress better than everyone. If you were one of my guy friends, would you think I was gay?

--SA

Dear SA,

Being able to be friends with girls and knowing how to dress are both really positive qualities and will actually help your love life a ton in the long run. And liking the O.C. does not in any way make you a social aberration -millions of people watch the show each week, both guys and girls, otherwise it wouldn't be on the air in the first place.

The fact that you're even asking me about this shows a little confusion in you, or at least some self-consciousness - which doesn't say anything about who you're attracted to, just that you need to get some more confidence and not worry so much about what other people are going to say.

Take care,
Jonathan

I have a problem. This guy, whose name is Jonathan too (go figure!) is in my second period class, and he's just adorable. Lately we've been flirting and I really like him. The thing is, when he started flirting with me, it was at the same time that I ended up with a cast on my ankle (I got injured during basketball practice; we both play.)

I don't know if he just feels sorry for me or if he's into me. Right now it looks like casual flirting, but I seriously need some advice. What do you think?

-Z

Dear Z,

No one can know for sure what this other Jonathan's motivations are except for him. But the fact is, attention from your crush is good - no matter what. Maybe he did feel sorry for you at first and thought you could use a little extra friendliness (though in my experience there's no such thing as disinterested attention,) but even if that's the case, it shows that he's a really nice guy.

My advice is to keep talking to him, and flirting with him, as much as possible. You can even use your disability to your advantage - ask him to carry your books for you one day; guys love to be the knight in shining armor. Mostly, though, just get to know him, and see if the casual flirting turns into anything more.

Take care,
Jonathan