Of course not, if he knows you're dating another guy, he sounds a bit conceited... Then again, I don't know him, but if I were guy #2, I'd never ask someone out if they were already dating someone else.

Totes true. Nice way of putting it. =)

If its greasy, don't go for it. If it isn't, rock on! Greasy hair freaks the daylights out of me. *shudder*

Fashion in the past has gone through many styles, like Victorian, Caveman, Vintage, Hipster, Rockster, etc. In the present, people are mixing up a lot of them, but they all call it, either one time or another, trendy. And like they say, fashion always repeats itself. ;)

Get to know her first, and then ask her sweetly, be a man, and say it face-to-face. =D Erm, and by the way, ask her out where? You're 9/10 years old, for goodness' sake. What would you do?