144 Questions to Ask Your Ex-Best Friend

When friendships end, we’re often left with a tangle of emotions and a suitcase full of questions. Whether you’re curious about what went wrong or you just want closure, it can be helpful to reach out to your ex-best friend and ask some questions. 

However, you must approach this conversation with caution and avoid coming across as judgmental, condescending, or angry. Instead, try to be respectful and understanding. With that in mind, here is a list of questions you can use.

Reflecting on the Relationship

  1. What do you think went well in our friendship?
  2. Can you recall a time when you felt we were at our best?
  3. How has our friendship impacted who you are today?
  4. In what ways do you think we influenced each other?
  5. What were your favorite shared activities or hobbies?
  6. Do you feel there was a turning point in our friendship?
  7. How do you think we’ve grown since we first became friends?
  8. Is there something you always wanted to tell me but never did?
  9. Did you feel understood and supported by me?
  10. What did our friendship teach you about relationships in general?
  11. Was there something you thought I should have done differently?
  12. How did you perceive me as a friend?
  13. Did you ever feel like I wasn’t there for you when you needed me?
  14. What positive traits did you appreciate the most in our friendship?
  15. Are there aspects of our friendship that you miss?
  16. Did we have a goal or dream that we didn’t accomplish together?
  17. In what ways do you think we changed each other’s lives?
  18. Looking back, what were our strongest attributes as friends?

Understanding the Fallout

  1. When did you first notice our friendship was starting to change?
  2. What do you think caused the initial rift between us?
  3. Was there a specific event that led to the end of our friendship?
  4. How did you feel during the times we disagreed or argued?
  5. Do you think there were signs of our friendship ending that we ignored?
  6. How could we have addressed our issues more effectively?
  7. Was communication a problem for us? If so, how?
  8. Did you try to reach out after the fallout? Why or why not?
  9. From your point of view, what could I have done to prevent the fallout?
  10. Did you feel I misunderstood something crucial about you?
  11. Were there unsaid things that piled up over time?
  12. How do you think external factors like work, family, or significant others affected our friendship?
  13. Do you believe there was a mutual mishandling of our issues?
  14. What was going through your mind the last time we spoke or argued?
  15. How did you process the end of our friendship?
  16. Was there a point where you thought things were beyond repair?
  17. How would you describe the weeks or months leading up to our last interaction?
  18. Looking back, what would you have done differently?

Personal Growth and Change

  1. How do you feel you’ve changed since we last spoke?
  2. What have been your biggest personal achievements since our fallout?
  3. Have you developed new perspectives or beliefs that have shaped who you are now?
  4. What life lessons did our friendship and fallout teach you?
  5. How have your goals and dreams evolved in recent times?
  6. Can you share a significant personal challenge you’ve overcome?
  7. What’s something new you’ve discovered about yourself?
  8. Has our breakup influenced your approach to new friendships?
  9. What have you learned about dealing with conflict and resolution?
  10. Have you found new hobbies or interests that have become important to you?
  11. In what ways have you worked on yourself since our friendship ended?
  12. How has the absence of our friendship influenced your growth?
  13. Have you had to let go of other relationships that no longer serve you? Why?
  14. Do you have any new practices or habits that have positively impacted your life?
  15. What does personal growth mean to you now?
  16. Is there a part of your identity that’s changed the most?
  17. How do you approach trust and vulnerability in your current relationships?
  18. What’s the most important quality you look for in a friend now?

The Current State of Affairs

  1. How would you describe your life at the moment?
  2. What’s currently taking up most of your time and energy?
  3. How satisfied are you with where you are in life right now?
  4. Are there any obstacles you’re facing that you’d like to share?
  5. How has your social circle changed since we parted ways?
  6. What’s something that’s happened recently that you’re really proud of?
  7. How do you generally feel about your past, present, and future?
  8. Is there a significant other in your life currently?
  9. Are there issues or concerns that you’re grappling with that I don’t know about?
  10. What does a typical day look like for you now?
  11. Have you made any big decisions or changes in your life?
  12. How do you spend your free time differently now compared to when we were close?
  13. What are your current passions or interests?
  14. Are there new people in your life that have become important to you?
  15. How do you manage stress or challenges these days?
  16. What are you most excited about for the future?
  17. Are there any goals or plans you’re actively working towards?
  18. How do you envision your life in the next few years?

Moving Forward

  1. What are your thoughts on rekindling friendships that have ended?
  2. Is there space in your life for our friendship now or in the future?
  3. What boundaries would you want to establish if we were to reconnect?
  4. How would you hope our interaction would be moving forward?
  5. What, if anything, would you want to be different in our friendship?
  6. Do you think we’ve each changed enough to start a new friendship?
  7. In what way do you think we could support each other now?
  8. Is there a form of communication you prefer for staying in touch?
  9. Would you be open to discussing the past, or would you rather move on?
  10. How would we address disagreements if they come up again?
  11. What’s the best way to approach sensitive topics between us?
  12. Would you want to establish new traditions or ways of hanging out?
  13. What would need to happen for you to trust me again as a friend?
  14. Are there any conditions under which you would not want to reconnect?
  15. How can we ensure that our past conflicts don’t repeat themselves?
  16. Can you envision a scenario in which our friendship could be even stronger than before?
  17. What’s the most important factor for you in rebuilding a friendship?
  18. Would you want to start fresh, or pick up from where we left off?

Revisiting Happy Memories

  1. Can you share a memory of us that still makes you smile?
  2. What was one of the most fun moments we had together?
  3. Do you have a favorite trip or event we attended together?
  4. Is there a particular inside joke that you still find funny?
  5. What song or movie always reminds you of our time together?
  6. Did we ever create something together that you’re still proud of?
  7. Is there an accomplishment or milestone we shared that you cherish?
  8. Have you ever passed by a place that reminded you of a good time we had?
  9. What was our silliest moment as friends?
  10. Do you still have any mementos from our friendship?
  11. Was there a time we supported each other that you look back on fondly?
  12. Have you ever told someone about a positive experience we had?
  13. What habits or interests did you pick up from our time together?
  14. Can you think of a time we laughed uncontrollably together?
  15. What was the best advice I ever gave you, and do you still follow it?
  16. Is there a lesson we learned together that you’ve carried with you?
  17. What was our favorite way to celebrate accomplishments or good news?
  18. Are there any traditions or routines we had that you miss?

Addressing Unresolved Issues

  1. Is there anything about our friendship or fallout you wish to resolve?
  2. Do you feel like there was a misunderstanding that needed clarification?
  3. Were there any actions or words you regretted after our split?
  4. Is there any hurt or anger you’re still carrying that we haven’t discussed?
  5. Did you feel you had the support you needed to voice your concerns when we were friends?
  6. What has been left unsaid that you feel is important for me to know?
  7. Are there any apologies that need to be made or received?
  8. How important is closure for you in this situation?
  9. Are there any specific scenarios that played out differently than you had hoped?
  10. Do you think there were assumptions made that need to be addressed?
  11. Was there external pressure on our friendship that we never talked about?
  12. How much did our other relationships (with friends or partners) impact what happened between us?
  13. Is there anything I did that you never got to question or confront me about?
  14. Are you looking for any acknowledgment of past events that we have left undiscussed?
  15. How can we talk about our unresolved issues in a constructive way?
  16. Do you feel like there’s a need for forgiveness in certain areas?
  17. Is there an area where you wish you had stood up for yourself more?
  18. What do you hope to accomplish by addressing these unresolved issues?

Future Interactions and Boundaries

  1. How would you prefer we navigate interactions if we see each other in social settings?
  2. In what ways can we ensure mutual respect for each other’s boundaries?
  3. What does a healthy boundary look like to you now?
  4. Are there topics or subjects you would prefer to keep off-limits?
  5. How should we handle any mutual friends or shared spaces we may have?
  6. Are you comfortable with regular check-ins, or would you prefer more space?
  7. How do you feel about acknowledging our past if asked by others?
  8. Is there a preferred way you’d like to communicate (text, call, social media)?
  9. Would you want to set any rules about discussing our friendship with third parties?
  10. How can we honor our past while respecting the present boundaries?
  11. What role, if any, do you see me playing in your life moving forward?
  12. How would you like to approach sharing personal information with each other?
  13. What’s your take on lending support during tough times, given our history?
  14. Are you open to checking in on significant dates, like birthdays or holidays?
  15. How might we respectfully decline invitations or interactions if needed?
  16. Would you be comfortable establishing a mutual understanding of privacy?
  17. How do we deal with potential conflict in our shared social circles in the future?
  18. Are you open to reassessing these boundaries as time goes on?

Frequently Asked Questions

Why do you think our friendship came to an end?

It’s tough to pinpoint a single reason why our friendship ended. I think it was a combination of factors—maybe we started to drift apart as our lives took us in different directions. We also seemed to have some misunderstandings that we didn’t fully address at the time, which probably created distance.

On top of that, as we grew as individuals, our interests and priorities might have changed, leading us away from the strong connection we once shared. It’s possible that we didn’t put in the effort needed to maintain our bond amidst these changes.

How did we both contribute to the issues?

Looking back, I see that we both played a part in our friendship’s challenges.

I may have been too quick to take offense and not vocal enough about my feelings at the time. Perhaps I didn’t listen as well as I could have to your concerns. On your end, there may have been times when you weren’t entirely open about what was bothering you, and that led to misunderstandings.

Together, we probably lacked the compromise necessary to work through our disagreements effectively.

Any unresolved feelings or words between us?

Yes, there was a situation that I feel was never fully addressed. When we had that big argument, I felt really hurt by some of the things that were said, and I never felt like we closed that chapter. I’ve always wondered if you truly understood why I was so upset, and I have carried some of that hurt with me. It might help me to hear your perspective on it now, to see if we can finally put that incident to rest.

Final Thoughts

Losing a best friend is hard, but it doesn’t mean the door is closed forever. If you’re having a hard time moving on, you should try to have an open and honest conversation with your former best friend. By asking those tough questions, you may be able to get the closure you need—or better yet, even find yourselves back to being best friends again someday!

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Jessa Claire is a registered healthcare provider. Music lover. Daydreamer. Thalassophile. Foodie. A hardworking Capricorn. Most days, an incurable empath. An old soul. Down-to-earth. Vibrant. When she's not writing, she can be seen relaxing with headphones on or engrossed in her favorite fan fiction book.