40 Questions to Help Evaluate Your Relationship

It’s almost Valentine’s Day. You might have mixed feelings about the holiday— especially depending on what your relationship status is. With so much focus on love around this time of year, now is a good time to reevaluate your relationship; maybe you’re just jumping in or maybe you’re wondering where your relationship is going. Wherever you are, we’ve got 40 questions to help you evaluate your relationship based on your partner’s answers.  

Easy Conversation Starters

1. What are three words your best friend would use to describe you?
2. Who are your closest friends? What do you look for in a friend relationship?
3. What’s your go-to karaoke song?
4. Is Valentine’s Day a real holiday?
5. What’s your perfect day?
6. If you had to do a Bachelor-style Hometown date, what would we do?
7. What did you to listen to on your way here? What’s your pump-up song?
8. If you could have dinner with anyone dead or alive, who would it be?
9. If money wasn’t a problem, what would you be doing with life?
10. If you could be great at any sport, what sport would you play? What league would you want to play in?
11. What movie/song/TV show/book describes me?
12. If you could improve on one of your skills, what would it be?
13. If you were a superhero, what would your superpower(s) be?
14. Would you rather wear the same outfit for a year or have to wear a new outfit every day for a year?
15. If there was a movie about your life, what would it be called and who would play you?
16. Who was your favorite teacher?
17. If you could adopt any famous pet, what pet would you adopt? 
18. What’s the ideal dessert?
19. What can you talk about for hours?
20. Would you rather win an Emmy, a Grammy, an Oscar, or a Tony?
21. What are your most off-brand and on-brand personality traits?
22. What’s your hottest take?
23. What is your dream Rom-Com-like moment that you hope happens to you one day?

The Deep Stuff

1. What takes your breath away?
2. What was your first kiss like?
3. Do you believe in love at first sight?
4. Where do you picture yourself in ten years?
5. What would I never guess about you?
6. Who is your role model?
7. What’s your biggest fear?
8. What would you say was your “first love”?
9. What’s the pain in me you wish you could heal (borrowed from Spirit and Muse)?
10. What’s your mantra?
11. What book has meant the most to you?
12. What are you looking for in a partner?
13. What are your giving and receiving love languages for a relationship? 
14. What’s one moment from your childhood that had the greatest impact on you?
15. What is your biggest secret? What have you never told anyone before?
16. What is one thing you do in your life because of a specific moment or person?
17. What’s one moment you’ll never forget?

If you’re still looking for more questions for your relationship, check out the New York Times has “36 Questions That Lead to Love,” to give you some more ideas. 

Happy Valentine’s Day to you and your loved ones!