To answer your first question, hell yeah
Guys love it when you initiate it, that's for sure, heck, I got my boyfriend that way
(2 years in september)
Secondly, just ask him out to eat or something simple like that. Food always gets them. *nods* When you're there, that's when you can cake on the crushin'. If he says no (which I doubt he'll do) then at least you asked. At least you'll know you tried
Plus if it doesn't work out for you immediately, he may go after you later, possibly next semester.
Good luck!!!
