change plans if you arrive at a restaurant and find it’s too noisy for a good conversation.
8. Are you close to your family? Or, tell me who’s in your family?
Why: Are they very involved with their family of origin? Is this something that appeals to you or not? Are their family intrusive?
9. Is there anything you don’t eat?
Why: Helps you plan future dates but also gives you an opportunity to choose not to pursue dating someone who has very incompatible food preferences from you.
10. Do you/have you ever smoked/drank/done drugs?
Why: You likely have a preference one way or the other.
11. Do you collect anything?
Why: Do they spend a lot of money or time collecting something?
12. How do you feel about…. [insert what you are most passionate about]?
Why: Whatever you’re really passionate about, do they respect it? For example, gaming.
13. Have you been to any good restaurants recently?
Why: Tells you something about whether they seek out new experiences.
14. What are your thoughts about the upcoming election (any upcoming election)?
Why: The main point here is not to jump to assumptions about your date’s politics. If you jump to an assumption that they have the same political views as you, they might feel too awkward to say that their politics are different.
15. When was the last time you really had fun?
Why: This gives you a glimpse into what the person really loves to do. Not just in their spare time, but really makes them happy. If it’s something strange, then you may want to back off.