I'm with you 100% on how hard it is to continue the coversation after the first question. I'm still working on it, but I was taught to think about the person's house. The house won't judge you. Plus it helps you remember what to ask. First, where is their house - "You live near here?" Then get curious about the house, who lives in it, why do they leave the house - "Been there long?" "Do you have kids? Are the kids still at home?" "Where do you work?" "What do you do when you aren't at work?"
Like I said, I am working on it and have a long way to go, but this idea has helped me. I think my W and I dated well because of a similar reason to you - my W was a social butterfly, so I didn't have to be.
