Some examples and samples: Are 당신 in any of my classes @ school? Do 당신 like cheese? What's your 가장 좋아하는 movie? Who do 당신 think would be a better President, Obama 또는 Romney? Do 당신 play football? Baseball? Basketball? Lacrosse? Hi. Hey. What kind of 음악 do 당신 like? What's up? What're 당신 doing this weekend? Which came first in your opinion, the chicken 또는 the egg? Yo.
if u hear him say anything about something u like, for example a tv-show, movie 또는 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'.
His 가장 좋아하는 movie His 가장 좋아하는 reality TV show His 가장 좋아하는 snack His 가장 좋아하는 electronic device 가장 좋아하는 game 가장 좋아하는 subject If he's in any of ur classes