Here's some background information:
So I've just recently come into the pickup community and only just started trying talking to women as more than friends. Overall, I have a fair amount of social skills but they are not the best; I think it's a product of my upbringing being an only child among other things.
My text game is solid; the extra few seconds to collect thoughts between messages gives me what I need to send out bomber texts. It's the in-person contact that I have trouble with.
Either way, I have begun to get better at speaking with people, but I always end up smacking into a brick wall when it comes to trying to hold a lengthy conversation. What are some of the things you guys do to fill in awkward silences, especially with a woman that is reserved?