Guide Me Wise Ones

So I’m a senior in college and I’ve been in a multitude of crappy relationships. Abusive ones to ones where I’ve been cheated on to ones that weren’t even real but just the guy getting what he wants. Recently I’ve been super interested in this guy and I’m always known for just running from trying anything because I don’t want to be rejected or it just turn into a one-Night-stand. My friend suggested that I just ask him one night if I can kiss him. Would that be stupid? Advice on a suggestion on what to do would be nice, please. Thanks.