25 Fun & Unique Date Questions

couple looking at fireworks
We all know the typical first date questions: “Where did you grow up?” “What do you do for work?” “Have you ever committed a felony?” However, one of our Boundless Insiders, Kelsey, asked our community for some fun and unique questions to ask when getting to know someone. Here are some of their answers and a few of our own:

1. What is your favorite part of your day? – Lara

2. What is the most adventurous thing you’ve ever done? – Katie

3. If you could live in any three cities in the world, which would they be and why? – Julie

4. What is your fondest childhood memory? – Kaitlynn

5. If you could instantly become an expert at something, what would it be? – Sarah

6. What is your favorite book (other than the Bible)? – Dale

7. What was your favorite game or toy as a child? – Joy

8. Where would you go if you could go anywhere in the world? – Erin

9. What is on your bucket list? – Bethany

10. If you could solve one world issue, what would it be? – Nicole

11. What is something you wish more people knew about you or don’t know that you’re good at? – Esther

12. What is something you’ve done in the last year that’s pushed you out of your comfort zone? – Sarah

13. What is your favorite episode of the Boundless show? – Boundless

Some other fun questions:

14. Have you ever changed your mind about something you were once sure about?

15. If you could invite any three people from history over for dinner, who would you choose?

16. What would your perfect day look like?

17. If you had to live in an ancient civilization, which one would you choose?

18. What is your favorite quote?

19. What is the most meaningful thing someone ever said to you?

20. If you could spend a day with any fictional character, who would it be?

21. Cats, dogs, other — or no pets?

22. Do you have a signature dish you can cook?

23. What personality tests have you taken and do you agree with the results?

24. If you could go back in time and do something differently, what would you change?

25. Would you rather live a month in squalor with your best friend or a year in luxury with someone you can’t stand? (Lisa Anderson suggested this one. Figures!)

The ability to ask (and answer) questions is a good area to grow in, as well as a mark of mature adulthood. In a world where many conversations take place on a screen, it’s important to know how to converse with an actual person – especially on a date.

Let us know what questions you would add to our list in the comments!

About the Author

James Clapper

James is Boundless’ project administrator, responsible for the fun social posts you see around the clock (some of these posts are actually useful, too, but we especially like the fun ones). He also does most of our content entry for the site, plus analytics, contracts, web maintenance, purchase requisitions, and anything else Lisa can think to foist on him. He’s also an artist, theologian, Jedi, LEGO master, children’s ministry director, husband and dad.