To some yes, but there are many who cannot get past the sheer stress of it. Remember that the teenaged period is one of the most confusing and most stressful times In life, and also the time of rampaging hormones...
I find it odd. I mean, she likes the shy type. He /is/ a nice guy. I prefer something more along the alpha male line... but that's more because if I feel like I can push them around, what fun is there in that?
See the thing is I just can't speak to girls I stutter and my brain starts to seize up, also I wouldn't really ask her out to dinner at my age 15 is a bit young for that...
Honestly, maning up, going up to her and talking to her is what needs to be done. If you can't even sum up the courage to talk to her, why should she waste her time with you? I don't mean to sound like an asshole. I apologize if I come off as that. However, as a man, this something that I wouldn't deem acceptable behavior from myself. Afraid? To speak to a woman? I'd feel, for a lack of a better word, a bit pathetic. Again, this is just something I'd feel if I were in your position. I wouldn't like myself if I did that. Fear is something that can be overcome, Zathos.
Ask her to dinner at your house. Or for ice cream, or coffee. Or just to study together then. Engage a woman mentally, be funny, and you're most of the way there.
If he can't build up the strength to directly ask, then what else is there to do? At that point you would not necessarily worry about being masculine