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20 Questions to Connect Deeper on a Date

Here are some questions to help you connect and have a great conversation with your significant other!

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You know date nights are important. All the big marriage experts say so, right? But sometimes life gets…chaotic. Your schedule fills up and circumstances out of your control make it impossible to get out of the house, let alone plan a nice evening with your spouse.

The following questions are designed to help you connect and have a great time no matter how big or small of a date you get to enjoy! Using the questions is easy, just alternate asking each other a question from the list. Pick any questions you like. The goal is to connect and have fun, not complete the list. Plus, you can always save the unused questions for future dates.

1. If Hollywood made a romantic comedy about us, who should play you and who should play me?

2. What’s your favorite outdoor activity we do together?

3. What is one of your favorite memories from when we were dating?

4. What is your favorite movie, book, or song?

5. What is one memory or event from your childhood that you’ve never told me about?

6. What do you want to do when we retire?

7. What is your dream job?

8. Which would you prefer, a lake house or a beach house?

9. What is your greatest talent?

10. What is something that scared you as a child?

11. Which did you like best—elementary school, middle school, high school, or college?

12. If you could have one superpower, what would it be?

13. Would you rather have more money or more time?

14. What was your favorite toy or possession when you were a child?

15. Do you prefer excitement or security?

16. If you could tell your younger self one thing, what would it be?

17. If you could only eat one meal for the rest of your life, what meal would you choose?

18. Is there a new hobby or activity you want to try?

19. When you were a child, what did you want to be when you grew up?

20. If you could have dinner with one famous person (still living), who would it be?

To see more of our content on dating, check out the message 3 Pieces of Advice for Dating Relationships from our series It's Complicated.

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