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55 Tough Relationship Questions That Will Make Your Bond Stronger

Asking hard relationship questions is crucial to foster a sense of trust and connection between partners

Asking your partner tough relationship questions is never easy, but what if we told you it could make your bond stronger? 

In her research on marital happiness, academic and relationship therapist Dr. Terri Orbuch followed over 300 couples over 30 years and found that when couples avoid difficult discussions — whether about money, religion, children, and in-laws — they’re less happy over time. 

Having difficult conversations gives you a chance to be vulnerable and lay all your cards on the table, which can help you and your partner grow closer. Although it might not be easy, asking hard relationship questions is crucial when it comes to fostering a sense of trust and connection between partners. 

When it comes to asking tough relationship questions, the most important thing to remember is to stay positive and lean into the topic. This is a chance to enrich your relationship and practice healthy communication skills. The more comfortable you are having uncomfortable conversations, the easier it is to overcome relationship road bumps down the line. 

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Tough questions for couples

  1. What topic do you find the most difficult to discuss with your partner? Why? 

  2. Does how you spend or save money cause any issues in your relationship? 

  3. How do you feel about how household chores are shared in your relationship? 

  4. Is there anything you’d like to change about your sex life?

  5. How do your religious or political beliefs differ? Does this cause tension?

  6. Is there anything you’d like to change about your relationship with your partner’s family?

  7. What are your top two expectations in your relationship?

  8. What are you not willing to compromise on in your relationship?

  9. Which behaviors are off-limits during an argument? 

  10. What counts as cheating to you?

  11. Are there any boundaries around work that you’d like to set?

  12. What aspects of your relationship do you expect your partner to keep private?

  13. Are there any boundaries you want to discuss with your partner?

  14. What have you found to be the most difficult aspect of your relationship?

  15. What is your biggest weakness as a couple?

  16. Do you feel your partner has ever broken your trust? If so, when? 

  17. What do you wish your partner understood about you?

  18. Are there any issues in your relationship that you feel are unresolved?

  19. Are you happy with how often you and your partner talk about your mental health?

  20. Do you think it’s ever ok to tell white lies in a relationship? Why or why not?

  21. How do you feel if you don’t orgasm during sex?

  22. Should bills be split equally based on how much you earn? 

  23. How do you feel about your relationship at the moment? 

  24. What goals would you like to achieve together?

  25. How do you foster friendship with your partner?

  26. If you could change anything about your past together, what would it be?

  27. What would you like your partner to open up about more?

  28. What have you not asked your partner about, but really should?

  29. When it comes to resolving conflict, what skills do you wish to get better at as partners?

  30. Are you happy with how much separate “alone time” you have in your relationship?

  31. What’s the biggest difference between you and your partner?

  32. What’s your and your partner’s biggest similarity? 

  33. What do you wish your partner did more to help you out?

  34. How can your partner best support you when you’re feeling low?

  35. Do you think you and your partner share the same values?

  36. Do you wish you and your partner had more interests in common? 

  37. Is anyone coming between you and your partner at the moment? Who and how so?

  38. What topic would you like to talk more about but don’t? Why not? 

  39. Which arguments tend to repeat in your relationship?

  40. Who apologizes first after having an argument? 

  41. If you could have one wish for your relationship this year, what would it be?

  42. What would you say is your partner’s biggest emotional need?

  43. Do you think you show each other enough gratitude?

  44. How secure do you feel in your relationship?

  45. How comfortable are you expressing frustration to your partner?

  46. Where do you see yourself in five years?

  47. What do you need the most from your partner right now?

  48. What’s something you agree to disagree on?

  49. If you could see into your future together, what would you like to know?

  50. What’s one thing you’d like to strengthen in your relationship?

  51. How can you display more equality in your relationship?

  52. How could you use the weekends to reconnect better together?

  53. What differences between you and your partner drive you nuts?

  54. What, if anything, makes you uncomfortable when talking about sex?  

  55. How can you grow together as a couple, so you don’t drift apart?

Looking for more tough relationship questions to bring you closer to your partner? Download the Paired app. 

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