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50 Challenging And Possibly Awkward Questions To Ask Your Partner

50 Challenging And Possibly Awkward Questions To Ask Your Partner

This post contains a list of challenging and possibly awkward questions to ask your partner.

Challenging And Possibly Awkward Questions To Ask Your Partner

1. What was your first impression of me?

2. How do you think your friends perceive our relationship?

3. What is something you’ve always wanted to tell me but haven’t?

4. How do you feel about the boundaries we have in our relationship?

5. What is one thing you feel our relationship is lacking?

6. How do we handle disagreements differently and how does that affect us?

7. What are your deepest fears about our relationship?

8. How important is financial stability to you in our relationship?

Related: Best 100 Let’s Get Deep Questions for Couples

9. What does commitment mean to you?

10. How do you feel about our intimacy and physical connection?

11. What is one thing you would change about our relationship if you could?

12. What keeps you up at night when you think about our future?

13. How do you really feel about my family?

14. What personal habits of mine do you find difficult to deal with?

15. How do you feel about the time we spend apart?

16. What aspects of your life would you like more privacy in?

17. How do you feel about the role of technology in our relationship?

18. What unresolved issues from past relationships still bother you?

19. What’s your honest opinion about my career and its impact on our life?

20. What insecurities do you have that you haven’t told me about?

21. How do you really feel about my friends?

22. What do you think about our communication style?

Related: +50 Questions To Rebuild Trust In A Relationship

23. Is there anything about your health that you haven’t told me but should?

24. How do you feel about the way we handle conflict?

25. What are your views on gender roles within our relationship?

26. How do you feel about taking care of aging parents in the future?

27. What are your deepest regrets?

28. How do you feel about our sex life honestly?

29. What is your biggest disappointment in our relationship?

30. How important is religion or spirituality to you in our relationship?

31. Do you feel I support your dreams and ambitions?

32. How do you feel about our plans for children?

33. What do you think about our spending habits?

34. What do you think are my blind spots?

Related: Best 50 Vulnerable Questions To Ask Your Partner

35. How do you feel about how we celebrate holidays?

36. Is there anything you feel too embarrassed to try with me?

37. How do we differ in our need for cleanliness and organization?

38. What do you think about my relationship with my exes?

39. What is one thing you wish I understood better about you?

40. How do you feel about our level of independence?

41. What personal sacrifice are you making for the sake of our relationship?

42. How do you feel about our levels of affection?

43. What are your thoughts on how we manage time together and apart?

44. How do you feel about the way I handle my anger or frustration?

45. What fears do you have about our relationship that you haven’t voiced?

Related: Top 100 Funny Dating Questions

46. What do you need from me that you feel you’re not currently getting?

47. How do you feel about the way I respond to your successes?

48. What thoughts do you have about our long-term financial planning?

49. How do you feel about how much we rely on each other?

50. What do you think are the biggest strengths and weaknesses of our relationship?

Related: Best 50 Ice Breaker Questions For Dating

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Conclusion

These questions can serve as important conversation starters that help both partners to address potential areas of conflict before they become problematic.

By Hadiah

Hadiah is a counselor who is passionate about supporting individuals on their journey towards mental well-being. Hadiah not only writes insightful articles on various mental health topics but also creates engaging and practical mental health worksheets.

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