26M, have my first date tomorrow with a woman 20 years older than me. I go on a lot of first dates and I feel like I’m pretty good at them, but all have been within one or two years of my age. Typically, I ask a lot about where they grew up, went to school, how they like the city, but also like to get into some deeper stuff about their families & dynamics like that. I feel like the bulk of these conversations revolves around themes of adolescence and transitions to adulthood.

Wondering if these topics of conversations would be less natural for someone in their middle aged years?

For anyone who has dated older women before drop some advice on what to finesse differently!