25 Valentine’s Day Questions to Ask

Instead of relying on conversation hearts, ask your Valentine some of these heartfelt questions. Valentine’s Day can mean different things to different people and may influence how you spend the day, whether as a centuries-old tradition or a holiday invented by greeting card companies.

Regardless of your approach, make use of the occasion to get to know your partner better. You might have been together for years, or just starting out, but Valentine’s Day is an ideal time to connect on a deeper level by asking each other questions.

Whether you prefer a fancy dinner or a cozy night in with a romantic movie, these 25 prompts will help you strengthen your relationship.

  1. What do you value more: careful planning or the freedom to be spontaneous?
  2. What’s your favorite karaoke song to sing?
  3. What’s your favorite childhood memory?
  4. What is your guilty pleasure TV show or movie?
  5. What’s the most romantic movie you’ve ever seen?
  6. If you could wake up tomorrow having gained one superpower, what would it be? Why?
  7. When do you think is the right time to say “I love you”?
  8. What is on your bucket list that we can do together this year?
  9. What’s your favorite way to receive affection?
  10. What’s one thing you’ve always been nervous to ask me?
  11. What was your favorite school lunch as a kid?
  12. What are three ways to make our relationship better?
  13. Who do you confide in more than anyone else?
  14. What’s your biggest dream for us as a couple?
  15. What’s the last song you saved to your playlist?
  16. How did we make each other smile this week?
  17. What’s one thing you always procrastinate on?
  18. If you could travel anywhere in the world with me, where would we go? Why?
  19. Where is your favorite place to be with me?
  20. What is the best outfit you’ve ever seen me wear?
  21. Would you rather ask for help or figure it out yourself?
  22. What soothes you the most on the back of bad news or a tough day?
  23. What’s a time we had together that you found the funniest?
  24. Who is your relationship role model? Your parents, a celebrity couple, or a friend? Why?
  25. How did you cope the last time you felt vulnerable?
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