You’re not crazy and he’s not clueless. He likes you, but I don’t think he wants to date you. He is probably aware of your crush, and he doesn’t want to come right out and reject you because he feels badly about the difference between the feelings he has for you and the ones you have for him. Sometimes people don’t want to hurt others, but by not being straight and clear, they end up confusing them. That’s what’s going on.
One of the things that might help you in the future is that if you let the guy do the asking out and the inviting on dates, you’ll have a lot more clarity about how much or whether or not he likes you. I know it can be frustrating because you have to wait for him to ask you — but you can give him a clue that you like him (whoever “him” happens to be) by flirting with him. This means smiling at him a lot, laughing at his jokes, complimenting him and letting him know you like him without coming out and telling him or asking him out.
I hope that helps!
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