120 Questions to Ask Your Ex-Best Friend

Losing a best friend can leave you feeling all sorts of things—hurt, confused, and maybe even a little stuck. The bond you shared was special and now it’s just…gone.

If you’re here, chances are you’re thinking about your ex-best friend—maybe you’re looking for closure, or maybe you’re wondering if it’s possible to patch things up. Whatever the reason, it’s not an easy conversation to start, but it could be worth it.

These questions are here to guide you through an honest and respectful conversation, no matter how things turn out. Whether it leads to closure or a fresh start, you’ll walk away with some peace of mind.

Questions for Seeking Closure

1. What do you think caused the fallout between us?
2. Do you feel there was a specific moment that changed our friendship?
3. Was there something I did that hurt you deeply?
4. Did I misunderstand your actions or intentions at any point?
5. Do you think the friendship could have been saved earlier?
6. What emotions did you feel during the fallout?
7. Was there a moment when you decided we couldn’t be friends anymore?
8. Do you think we outgrew each other as friends?
9. Were there signs that our friendship was struggling before the fallout?
10. Did our friendship make you feel valued while it lasted?
11. Do you think external factors affected our friendship?
12. Was there something you wanted to tell me but never did?
13. Do you feel like I listened to you enough when we were friends?
14. Were there expectations I failed to meet as your best friend?
15. What do you think I could have done differently?
16. Do you think we should have communicated better before things fell apart?
17. Was there someone else who influenced our fallout?
18. Looking back, do you regret how things ended?
19. Do you think we both shared equal responsibility for what happened?
20. Is there anything you want to say to officially close this chapter?

Questions to Express Unsaid Feelings

1. I wish I had told you earlier how much our friendship meant to me—do you feel the same?
2. I’m sorry for the hurt I caused—how did it affect you?
3. I regret not being there for you during [specific event]. How did you feel about that?
4. I miss our friendship—do you ever miss it too?
5. I wish I had apologized sooner. Do you think it would have made a difference?
6. I feel sad about how things ended—do you feel the same way?
7. I want you to know I always admired your [specific trait]. Did you know that?
8. I never told you how grateful I was for [specific memory].
9. I wish I had been more honest about my feelings back then—does that surprise you?
10. I regret the things I said in anger—do you remember them?
11. I hope you know I valued you as my best friend. Did you ever doubt that?
12. I always felt like I could rely on you—did you feel the same about me?
13. I still think about the good times we shared—do you?
14. I feel like I let you down—how can I make amends?
15. I want you to know that I forgive you for [specific incident]. Can we move past it?
16. I’ve been holding onto guilt about [specific action]—did it hurt you?
17. I wish I had celebrated your achievements more. How did you feel about my support?
18. I want you to know you taught me a lot about [specific life lesson].
19. I still care about you deeply—does that surprise you?
20. I hope we can part ways with peace if nothing else. Would you agree?

Questions to Understand Their Perspective

1. How did you feel during the hardest times in our friendship?
2. Did you feel supported enough by me as a best friend?
3. Were there things you needed from me that I didn’t provide?
4. What made you feel happiest in our friendship?
5. Did you feel like I understood your needs?
6. Were there things you wanted to tell me but couldn’t?
7. How did my behavior affect you during the fallout?
8. Did you ever feel like I prioritized other things over our friendship?
9. Were there moments when you felt alone in the friendship?
10. Did I ever unknowingly hurt you with my words or actions?
11. Did you ever feel like I wasn’t being genuine with you?
12. What was your perspective on our final argument or disagreement?
13. Did you feel like I respected your boundaries?
14. Were there moments when you doubted our friendship could last?
15. How did our fallout affect your life overall?
16. Did you ever hope we’d reconcile?
17. Was there anything I misunderstood about you as a person?
18. Do you think I knew you well as a friend?
19. Was there a particular incident that stood out as the breaking point for you?
20. If you could share one thing about your experience with me, what would it be?

Questions for Self-Reflection

1. What role did I play in the fallout of our friendship?
2. Did I fail to notice signs that you were unhappy in the friendship?
3. Was I as supportive as I could have been?
4. Did I listen to your concerns or dismiss them?
5. Was I too focused on my own needs during our friendship?
6. Did I hold onto grudges instead of resolving conflicts?
7. Was there a moment when I could have apologized but didn’t?
8. Did I respect your boundaries as a friend?
9. Was I honest with you about my own feelings?
10. Did I take you or our friendship for granted?
11. Was I a good communicator, or did I expect you to read my mind?
12. Did I let external factors affect how I treated you?
13. Was I patient and understanding when you needed me to be?
14. Did I make you feel appreciated and valued as a friend?
15. Was there a pattern in my behavior that could have hurt you?
16. Did I project my insecurities onto our friendship?
17. Was I open to your perspective during disagreements?
18. Did I compare our friendship to others unfairly?
19. How can I grow as a person from this experience?
20. What lesson can I take from this friendship to improve my future relationships?

Questions to Rebuild the Friendship

1. Are you open to rebuilding our friendship?
2. What would rebuilding our friendship mean to you?
3. Do you think we can truly move past what happened?
4. What boundaries should we set moving forward?
5. How can we rebuild trust between us?
6. Are there specific things you’d like me to work on if we reconnect?
7. What can I do to show you that I’m committed to making things better?
8. Do you feel comfortable opening up to me again?
9. How do you think we should address lingering issues?
10. What changes do you think we need to make for this friendship to work?
11. Are there any triggers from our past friendship we should avoid?
12. How can we make sure history doesn’t repeat itself?
13. Do you think rebuilding our friendship will be worth the effort?
14. Should we set some expectations for how often we connect?
15. Do you want to take things slowly or jump back in fully?
16. What’s one thing you miss about our friendship?
17. How can I support you better as a friend this time?
18. Do you believe we can grow from this experience together?
19. What do you hope will change if we reconnect?
20. Can we both promise to communicate more openly going forward?

Questions About Their Current Life

1. How have you been since we last talked?
2. What’s the most exciting thing happening in your life right now?
3. How has work/school been for you recently?
4. Have you traveled anywhere new or exciting?
5. What’s one new hobby or interest you’ve picked up?
6. How is your family doing?
7. Have you been spending time with new friends?
8. What’s one thing you’re looking forward to in the future?
9. Are you working on any personal goals or projects?
10. How are you taking care of yourself these days?
11. Have you read or watched anything interesting lately?
12. What’s one accomplishment you’ve been proud of since we last spoke?
13. Are there any challenges you’ve been facing?
14. How has your perspective on friendships changed since our fallout?
15. Are there new traditions or routines in your life?
16. What’s one thing you’ve learned about yourself recently?
17. Have you reconnected with anyone else from your past?
18. What’s something small that’s been bringing you joy?
19. Are there any upcoming events or plans you’re excited about?
20. How can I support you in your current journey?

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Frequently Asked Questions

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Final Thoughts

Reaching out to an ex-best friend isn’t easy, but it can be worth it. It’s a way to show that you care enough to have an honest conversation, even if it feels a little awkward at first.

Remember, this is about clarity and healing—for both of you. It’s okay if things don’t go exactly how you hope. What matters is that you tried, and that alone can bring you a sense of peace.

Friendships, like people, change over time, and it’s all part of life. Whatever happens next, you’ll know you did your best to handle it with care.