<human>: Condense the text into a few key points

Alright so I turn 20 in January and I've only had one relationship, which lasted 7 months.

Recently (being the last few months) I went on a date with a girl from college and well.. clearly that didn't turn out well.

My problem, I think, is that:
1) I am an extremely nice guy. I listen a lot and am very shy around girls. 
2) I over think things frequently.
3) I look way younger than I actually am, which I attribute to girls not taking me seriously in my attempts.

How do I go about asking a girl out? If looking younger than I am is the problem, how do I simply "ask a girl out"?
Secondary question: Is it creepy to ask a girl, who is working where you're doing (x) activity, out or for her number?
<bot>: Shy, really nice, apparently look about 14 or 15 instead of 19, almost 20. How do I go about asking a girl out?