I don't know if you should discuss politics until you really know the person. People get offended too easily. Not that you would care if you were secure about yourself, but that is a subject for another thread.
If anything, this should be considered a practice date. You really need more practice so you don't have to overanalyze the situation as much as you do. Get this under your belt, and make sure you're looking for other opportunites with other women. It's the only way you'll start to feel more comfortable with yourself, and when you're comfortable, she's comfortable. I can already tell there's going to be a few awkward moments on this date. I know it's cliche, but you need to try to be yourself. Pretend she's a guy, and talk about things that interest you.
If anything, this should be considered a practice date. You really need more practice so you don't have to overanalyze the situation as much as you do. Get this under your belt, and make sure you're looking for other opportunites with other women. It's the only way you'll start to feel more comfortable with yourself, and when you're comfortable, she's comfortable. I can already tell there's going to be a few awkward moments on this date. I know it's cliche, but you need to try to be yourself. Pretend she's a guy, and talk about things that interest you.