Some examples and samples: Are Ты in any of my classes @ school? Do Ты like cheese? What's your Избранное movie? Who do Ты think would be a better President, Obama или Romney? Do Ты play football? Baseball? Basketball? Lacrosse? Hi. Hey. What kind of Музыка do Ты like? What's up? What're Ты doing this weekend? Which came first in your opinion, the chicken или the egg? Yo.
if u hear him say anything about something u like, for example a tv-show, movie или video-game u could always start talk to him about that. then it won't seem like you're desperate :) u just want to talk about the awesome thing he brought up to begin with. don't think it'll work unless u hang out in the same circles though... 'cuz if u don't it might seem wierd to just jump into a conversation, just sayin'.