The key is to not let opportunity pass you by. My job calls for occasional trips to out of town and many times lands myself and coworkers in college towns. My buddies talk big game but would never approach women how I would whenever we were out and about. The key is confidence, give a few less fucks than the average male, and not sound like you need more practice having hypothetical conversations with youself in the bathroom mirror be fluid with whatever possible direction the conversation could go.
I gave up being the guy who always wondered "what if" at a house party at age 21, and never looked back...well except now because I'm married...but you know what I mean.