[Andrew]

I’d like to share a two part answer based on experience. If it is someone local and there is a chance you will have another meeting inside of seven days, then maybe surface topics or local area attractions is a nice start. If it is a long distance relationship and you have the opportunity to meet, you may feel pressured and short on time. Questions about personal habits and family matters may be more in line.

I’ve always thought “Are you on the FBI’s Most Wanted List?” is a nice ice breaker. (That’s my sense of humor)

[Unknown Member]

Where do you see yourself in 5 years? I know that is what a future employer would ask in an interview. I find that will tell a lot about a person. I myself would stick a lite conversation and see where it leads. Nothing heavy yet I want to get to know the person better. We do this with friends that we just met. But on a date I would assume, I know a bad word, that you already know something about the person prior to the date or else why would even ask them out on a date?

[Sarah-Mark]

That is a great question and can help with building the relationship and even learning more about them. Especially if you are listening to their answer.