I don't fear rejection, not one bit. I've been rejected my entire life, and I'm aware that it's nothing serious, yet I'm still afraid of approaching and I can't understand why. However, if I ever get the balls to approach, and I ask her what program she's in at my college, what she does, if she likes it, ask her what she likes to do for fun, then how do I eventually escalate into conversation that's actually enjoyable? Or do I simply ask her all those boring questions, then her number, then worry about the potential date? Even so, let's say I manage to get to that dating phase, what do we talk about then? I just can't seem to figure out how to make conversations be fun.

ALSO, the most awkward part is after we've had that mini, boring interview like conversation, I'll most likely see her the next day, and that makes this entire thing so difficult for me because then I feel obligated to talk to her, AND I DO want to talk to her but my fear is that I'll have nothing to say. I'm not sure how to be fun with new people, it takes a lot of time for me.