Valentine’s Test: How To Find Out If You Have A Keeper This Valentine’s Day

How do you know if the person you’re dating is a keeper?

I get this question all the time from clients, conference goers – even from friends. And when Valentine’s Day comes around, many people are drawn to evaluate their relationship compatibility and happiness.

There’s something about watching a sea of couples descend upon local restaurants, bars and bistros that makes you wonder, “Are they happy?” and then comes the inevitable, “Are we happy?”

In order to help couples evaluate their relationships more easily this Valentine’s season, I’ve come up with a list of questions that will not only provide food for thought, but might even initiate a communication breakthrough. It always amazes me how couples can go for weeks, months, even years without diving deep and connecting on core values, beliefs and goals. I’ve even counseled newlyweds who are shocked to discover they don’t agree on whether or not to have kids.

You don’t need to barrage your lover with all 50 questions at once, but scan the list for the ones that stand out to you. For example, maybe you already know how your partner likes to relax, but you’d love to know when they last had a good cry, or what they consider their most prize possession.

This list is good for couples who have just started dating, or are in a relationship. Going through this list with your lover helps you learn more about each other, opens up communication and creates intimacy.

Explore these Valentine’s Day compatibility questions together:

  1. What is the worst thing a past date could say about you?
  2. What is your most precious possession?
  3. List the best qualities you have to bring to a relationship.
  4. Do you think you need to make any personal improvements? If so, what?
  5. What are your biggest fears about relationships?
  6. Who has been the most influential person in your life and why?
  7. Apart from your appearance, what is the first thing that people notice about you?
  8. What is one thing that people do not notice about you right away that you wish they would?
  9. What are 3 things that you cannot live without?
  10. What is your definition of intimacy?
  11. What was the most fun date you ever had?
  12. What is your favorite way to relax?
  13. What disgusts you?
  14. When was the last time you cried?
  15. What do you like to spend money on?
  16. How much money do you need a year to be comfortable?
  17. How would you describe a perfect date?
  18. What 3 qualities must your partner have?
  19. What is the worst habit that you have?
  20. What would you do if you and your partner had a mismatched sex drive?
  21. Describe yourself in one word.
  22. What makes you angry?
  23. Would you say that you are more dominant or submissive?
  24. Who or what do you love?
  25. What do you feel is the biggest success you have achieved in your life?
  26. How many times have you been in love?
  27. Would you rather your partner was funny, seductive, smart or nurturing?
  28. When do you feel most vulnerable?
  29. What lessons have you learned from past relationships?
  30. What is a relationship deal-breaker for you?
  31. What was your most embarrassing relationship moment?
  32. What is your favorite part of your body?
  33. What’s your favorite romantic, sensual or sexual activity?
  34. What makes you believe that you are ready for a relationship?
  35. What turns you on?
  36. What turns you off?
  37. What’s the best compliment you’ve ever received?
  38. What’s the most hurtful criticism you’ve ever received?
  39. Are you fanatical about anything?
  40. What is the biggest failure or drawback you have ever experienced?
  41. Can you overlook anything from your partner’s past?
  42. Do you have any inhibitions?
  43. What do you love about yourself the most?
  44. What are you not willing to change for a relationship?
  45. What do you think are the benefits of being in a relationship?
  46. Do you believe in monogamy?
  47. How do you feel about having kids?
  48. If we have kids, what would your parenting style be?
  49. What would you do if your partner became physically disabled?
  50. What scares you?

Try Self-Discovery Instead:

If you’re feeling nervous about launching into this kind of couples’ self-discovery, try answering the questions just for yourself at first, and see what comes up for you. Grab a journal and write down your answers to whichever questions pique your interest, and let your feelings flow freely, without judgment. Insight into your own opinions and personal choices can only help foster clarity within the relationship, plus you’ll be one step closer to opening up a mutual dialogue and taking your intimacy to new heights.

May all your Valentine’s wishes come true!


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