Guys think the same way when they are interested in a girl...
Try these ideas:
1.) Do any of your friends know him well? Maybe you 3 or w/e could hang out and then she has to leave early or something and u 2 hang out.
2.) Not sure what type of personality you have. For example, one of my friends can walk up to a girl and simply say that he likes her and ask for her phone # right there, so you think of a way that fits your personality
3.) When you see him in the hall way strike up a conversation that makes him feel comfortable. An example from personal experience is when a girl likes a shirt of mine or w/e and says "Hey cool shirt, where is that from?" I get a little comfortable around them and answer of course. Then just keep the conversation going like "Oh cool, never heard of the place, thanks. Me and my friends are going shopping this weekend, maybe you can show me around the store?"
I am like you, afraid to look stupid when I talk to certain people, but think of it this way. Imagine someone is talking to you, and that person is saying what you want to say. It doesn't sound so stupid does it now? It sounds normal, and now imagine your thoughts that occur after this person says what he says. That's probably what the boy will think, that you are just being nice and like him.
Or in other words, things always seem stupid, until someone else does it, then it doesn't seem so bad. Do you know what I mean?
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