Katie,
this is a really hard thing to get over. but it doesn't mean that you can't! being shy does have it's advantages sometimes, but most of the time, it's just plain annoying! (trust me, I've been there). my boyfriend sometimes gets annoyed with me when I have nothing to say. he tells me just to talk about anything, and that it doesn't matter if it's about something stupid, like about my hair or anything! so if he really cares about, he won't care what you talk about, as long as you talk! it's not too hard! hope I helped a bit!
Lissa