There's this thought that occurred to me probably a couple years ago (I'm 28 now) and it's one of those thoughts that I wish had occurred to me much sooner, but I swore if I got the chance I would spread this message to anyone who could benefit from it. Here's the thought:
At some point, school ends and you will never see most of these people ever again for the rest of your life.
If I had realized that when I was in high school, I would have asked out every girl I ever had a crush on -- but I only ever asked out three. A PALTRY THREE! OUT OF FEAR!
My friend, there is not a single guy at your school who hasn't been in the EXACT same predicament you're in now. Take comfort in that.
Take comfort, also, in the fact that you are in the BEST dating situation OF YOUR YOUNG LIFE! Even if this girl were to make a horrifying display of just how much she DOES NOT want to give you her number and how terribly UNWORTHY you are of calling said number (unlikely, given that you said she laughs at your jokes), what would it matter? In a few more years, you're out of there. And she's history. She's a funny story you'll tell your college buddies -- a story that begins with you having the guts to approach her in the first place.
A quick example: when I was a senior in high school, I had a mad crush on this girl... she was so fine and for some reason she enjoyed my company. I entertained the idea of asking her out but never did. I rationalized that decision with the usual "she'll probably turn me down", "what if I scare her off" type thoughts. Recently, she called me up and we talked about the old days and she told me that during that same time she had a crush on me. THIS BLEW ME AWAY.
The lesson: DON'T BE ME.
Ask this girl for her number. If she asks why, tell her it's because you like her and you think she's pretty. Be direct. It will blow her mind.
And finally (sorry for the book, here, fella), think about how this benefits you in the long run, even if dating this girl doesn't pan out. You keep it up with this direct approach with girls you like right now and in a couple of years when you're in college, you'll have no reservations approaching the ladies. You'll actually feel comfortable about it.
Good luck, squire.
