How to ask a shy/nerdy guy out?

if he likes you the cliques wont matter. group vs single is a double edged sword. one on one he may feel pressured that since youd pay more attention to him you might be judging him more than in a group. but groups are more intimidating and would probably cause him to be more shy. i think id say one on one would be better starting out though. jus be real nice open and patient and soon enough that whole shy thing will be completely gone =)