1. What are some of your hobbies?
This will help you see what things your date finds fun and interesting. Your date may spend a lot of time on these hobbies, and if you get serious, may want to involve you in these activities.
2. How did you choose your career?
Most people have interesting stories to tell about how they landed on their chosen career path. A discussion about careers may help you learn more about their motivations and work ethic.
3. What are you most passionate about?
Your date’s passion will be where much of his or her time and energy is spent.
4. What are some of the goals on your bucket list?
This can provide some insight into areas of your date’s life that have yet to be explored.
5. How long ago was your last serious relationship?
The timing may show you whether your date is ready to begin another relationship. If it was very recent, you may want to explore why he or she is dating so soon.
6. What was the reason your last relationship didn’t work out?
Also ask who initiated the break-up and why. This may give you some insight into how he or she handles conflict and what they find important in a relationship. In addition, how was the news delivered? If your future partner says it was via text, email, or worse — social media — you may want to proceed with caution. Someone that insensitive will likely treat you the same.
7. What’s your biggest relationship regret?
Did he or she wish they spent more time with their ex? Did they fight all the time? Ask what your date would have done differently.