30 Valentine’s Day Questions – Valentine’s Questions for Couples


Like each relationship, Valentine’s Day looks different for everyone. Whether you believe the holiday was invented by greeting card companies, or feel it’s a sacred, centuries-old tradition can impact how you spend February 14.

This year, no matter how you decide to celebrate (or not celebrate) the holiday, use it as an opportunity to get to know your partner a little better. Maybe you’ve been dating for decades, or the relationship isn’t even Instagram official yet. Either way, Cupid’s birthday is a great time to dive deep by asking each other a few questions.

Choose to swap stories over a fancy 5-star dinner or cuddled up on the couch with your favorite cheesy rom-com. No matter where you are in your relationship, these 30 prompts will help strengthen it.

  1. When do you think is the right time to say “I love you”?
  2. When’s the last time you felt vulnerable? How did you cope?
  3. What is your favorite birthday you ever had? Why?
  4. Who do you confide in more than anyone else?
  5. What do you value more: careful planning or the freedom to be spontaneous?
  6. If you could meet one celebrity, who would it be?
  7. What soothes you the most on the back of bad news or a tough day?
  8. What was your favorite school lunch as a kid?
  9. What is the best outfit you’ve ever seen me wear?
  10. Would you rather ask for help or figure it out yourself?
    couple having fun on a date in the early morning hours

    Christopher Malcolm

  11. What’s your favorite karaoke song to sing?
  12. What’s the most romantic movie you’ve ever seen?
  13. What’s your biggest dream for us as a couple?
  14. What’s your favorite childhood memory?
  15. What’s one thing you always procrastinate on?
  16. Where is your favorite place to be with me?
  17. What’s your favorite way to receive affection?
  18. What is your guilty pleasure TV show or movie?
  19. What three words would your best friend use to describe you?
  20. If you could travel anywhere in the world with me, where would we go? Why?
    portrait of romantic african american couple celebrating love


  21. What are three ways to make our relationship better?
  22. If you could wake up tomorrow having gained one superpower, what would it be? Why?
  23. What is on your bucket list that we can do together this year?
  24. How did we make each other smile this week?
  25. Would you surprise me with an expensive gift, or would you consult me before spending the money on it?
  26. What is the last song you saved to your playlist?
  27. Is there any goal you want to accomplish that I can help you with?
  28. What’s a time we had together that you found the funniest?
  29. Who is your relationship role model? Your parents, a celebrity couple, or a friend? Why?
  30. What’s one thing you’ve always been nervous to ask me?


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