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38 Core And Important Relationship Questions To Ask Your Boyfriend

Asking your partner these relationship questions is critical to creating a lasting relationship. Whether your relationship is brand new, or you have been together for a while, asking questions – both serious and fun – is a great way to get to know your partner and spark meaningful conversation.

relationship questions to ask your boyfriend


1. How did your last relationship end?

2. Are you and your ex still friends?

3. How many sexual partners have you had?

4. Have you put yourself at risk for an STD by skipping protection?

5. Have you been tested for STDs/HIV?

6. Would you be willing to go in for testing again before we get more involved?

7. How would you handle it if you thought another guy was hitting on me?

8. How do you cope with stress?

9. Do you have any bad habits I should know about?

10. What’s the worst thing you’ve ever done?

11. Have you ever broken the law?

12. How would you handle it if you lost your job?

13. How would you handle it if I lost my job and we were living together and sharing expenses?

14. Are you able to keep your anger under control?

15. Do you like to travel or would you rather stay home?

Also Read: For Ladies: 5 Questions That Create Connection On A First Date

16. How do you handle disagreements?

17. Do you think men and women can be platonic friends?

18. Do you think it’s okay for men and women who are in separate relationships to go have coffee or lunch together?

19. What is something that you do that could possibly cause me to question your loyalty?

20. What are some of your ideas for how to keep a relationship strong over time?

21. What do you think of my dream of becoming a ______? (Fill in your own goal, like novelist, karaoke star, or TV personality.)

22. Do you think it’s okay for people to vent to others about their significant others, or do you think that it’s completely disrespectful and complaints should be kept within the relationship?

23. When you break up with someone, how do you do it?

24. What’s the worst break-up you’ve ever experienced? Why was it so bad?

25. What are your thoughts on marriage?

26. What are your thoughts on divorce?

27. What do you consider cheating, besides the obvious?

28. Are you comfortable talking about where our relationship is going?

29. If I were offered a promotion and had to move away, would you move with me?

Also Read: Single Women: 7 Proven Strategies For Meeting Your Mr. Right

30. Where do you see us in five years?

31. If a girl asked for your number, would you give it to her, just in case we break up?

32. If one of my friends flirted with you, would you tell me?

33. If one of your friends or family members told you to break up with me because he/she didn’t like me, would you?

34. How do you feel about my family and/or friends?

35. How would you deal with a disagreement with one of my family members or friends?

36. How much time do you think we should each spend with our family/friends outside of gatherings that require us both to be there?

37. What do you tell your friends about me when I’m not around?

38. If one of your friends flirted with me and I told you about it, how would you handle it?

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