This will scare the person off since it seems you’re getting too personal too fast. An initial conversation should discuss topics like movies, trips around the world, concerts, favorite restaurants or foods, or the environment. Ask him about where he grew up, what his favorite sports team is. Flirting is like a child’s game of hide and seek or a back and forth tennis match; most of the exhilaration of getting to flirt comes from what is hidden and what is revealed, all in the right, sexy timing. Don’t rush it and enjoy the ride.