I can usually get the girls that I interact with frequently (sit by me in class, are in the same clubs, etc.) to have legitimate, I joke about you and you joke about me kind of conversations. I'm alright at first impressions, but it's really once someone gets to know me that they really start to like me.

The thing is that when I start talking to a new girl I approach I can never get past the "where are you froms" and when I do, it's conversation that's too deep and feels unnatural (life goals, dreams, you know). What can I do?