41 Questions to Ask Your Boyfriend About His Ex

Part of getting to know your new boyfriend better is learning about his past relationships. His relationship history can give you what he wants in a partner as well as provide red flags for things to look out for. Asking your boyfriend questions about his ex can be a minefield, though. You don’t want to seem jealous or insecure, but you also want to know if he’s over his ex and if she might still have feelings for him. 

Some of these questions are lighthearted, while others are more serious. Whichever way you go, these questions will help you start a conversation that will give you a better understanding of who your boyfriend is- and who he has been.

41 Questions you can ask your boyfriend about his ex:

  1. How did you meet?
  2. What was your first impression of her? 
  3. How long were you together?
  4. Why did you break up?
  5. How does she feel about the breakup? 
  6. How do you feel about the breakup? 
  7. What was the hardest part about the breakup? 
  8. Would you describe her as a good partner?
  9. What did you learn from your relationship with her? 
  10. What did she teach you about relationships? 
  11. Do you still keep in touch? If so, why?
  12. What was your favorite thing about her?
  13. What was your least favorite thing about her?
  14. Did she ever cheat on you? 
  15. Did she ever lie to you? 
  16. Did she ever hurt you emotionally or physically in any way?
  17. Was she jealous, possessive, or controlling? 
  18. Have you ever met her family or friends?
  19. What were they like?
  20. What are the things you disagreed on most?
  21. Has she ever apologized for anything she did during the relationship? If so, what did she apologize for? 
  22. Was there anything you liked to do together that you no longer do?
  23. What things did she do in the past that annoyed you?
  24. Do you think about her often? If so, why?
  25. Is there anything you miss about her?
  26. Does she have any qualities you look for in a lifetime partner? 
  27. Would you ever get back together with her? Why or why not?
  28. Does she ever bring up the thought of getting back together with you? If so, what do you say? 
  29. Do you think she has been seeing someone new since you broke up? 
  30. Does she have any hobbies or interests that she is really passionate about? 
  31. Do you have any mutual friends? 
  32. If so, do you still see them often?
  33. Is there anything in your relationship with her that you would do differently if you had the chance?
  34. What are the positive things that come to your mind when thinking about her?
  35. What are the negative things that come to your mind when thinking about her?
  36. How have your relationships with other people changed since being with her?
  37. Does her name come up often in conversations with friends or family? If so, in what context does it usually come up and how do you feel when it does? 
  38. Do you think of her more often during certain events or holidays than others (e.g., birthdays, anniversaries, etc.)? If so, how do these events affect you emotionally and how do you deal with them when they come up each year?
  39. When events in your life are good or bad, do you think about them more or less? 
  40. Does she still play a role in your life?
  41. What do you think I can learn from her?

Frequently Asked Questions

Does the past matter in a relationship?

The past can certainly play a role in a relationship, especially if there are unresolved issues from the past. If either person in the relationship is still carrying around baggage from past relationships, it can be difficult to move forward. The past can also affect how we view our current relationship and can cause us to make assumptions about our partner that may not be accurate. It is important to try to let go of the past and focus on the present and the future.

How can you tell he’s not over his ex?

There are a few telltale signs of whether or not a man is still hung up on his ex. If he’s constantly talking about her, comparing every new girl to her, or constantly bringing her up in conversation, then it’s pretty clear that he’s not over her. Another indication is if he is not ready to move on and start over with someone new. If he’s still stuck in the past, it’s probably not going to work out between him and you.

How can you stop overthinking about your boyfriend’s ex?

It can be hard to stop thinking about your boyfriend’s ex, especially if you feel like she’s still in the picture. One way to stop is to remind yourself that you are the one he is with now, and focus on building a strong relationship with him. Also, try to keep yourself busy with other things – this can help take the focus off her. Ultimately, it will take time and patience to stop overthinking about your boyfriend’s ex; but if you work on yourself and stay positive, you can overcome this obstacle.

Can you be friends with your boyfriend’s ex?

There is no definitive answer to this question because every relationship is different. Some couples can be friends with their partner’s ex without any issues, while for others it can be more difficult. Ultimately, it comes down to communication and understanding between the couple.

If both partners can agree that they want to be friends with the ex, and can deal with any potential awkwardness, it is possible. However, if either partner feels uncomfortable or threatened at the thought of being friends with the ex, it’s probably not a good idea.


Now that you’ve asked your boyfriend all these questions about his ex, it’s time to sit back and listen carefully to his answers. His answers will give you valuable insight into who he is and who he has been in past relationships.

They’ll also help improve communication in your current relationship, as you better understand what he likes and dislikes in a partner. With this knowledge, you can avoid repeating negative patterns from his previous relationships and build a more positive and fulfilling relationship with him!

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