340 Questions to Ask Your Ex Best Friend

Navigating the waters with an ex-best friend can be tricky, but sometimes life gives you a second chance to mend fences or find closure.

Whether it’s been months or years, asking the right questions can open the door to meaningful conversations. From uncovering shared memories to understanding how you’ve both changed, these questions are your roadmap to deeper insights.

About Their Feelings

1. How have you been feeling lately?
2. Do you ever think about our time as best friends?
3. What emotions come up when you think of our past?
4. How did you feel when we started drifting apart?
5. Did I ever do something that hurt you?
6. What moments between us meant the most to you?
7. How did you feel when we stopped talking?
8. Do you ever feel like there were things left unsaid?
9. What have you missed most about our friendship?
10. How do you remember the good times we had?
11. Are there any regrets you have about our friendship?
12. Do you wish things were different between us?
13. How do you cope with feelings of loss or nostalgia?
14. Was there a moment you felt our bond breaking?
15. How have your feelings evolved over time?
16. Are there things you wish you could tell me now?
17. How did you feel when you saw me with other friends?
18. Do you believe in second chances for friendships?
19. What was your first reaction when we started to drift apart?
20. Did you ever feel misunderstood in our friendship?
21. What emotions do you associate with our best moments?
22. Have you found closure with how things ended?
23. Do you feel like we could have handled things better?
24. Do you ever reminisce about our memories together?
25. How have you been healing from the hurt?
26. Are there moments you wish we could relive?
27. Do you ever regret not reaching out sooner?
28. How do you perceive my role at the end of our friendship?
29. Do you wish we had communicated more?
30. What are your feelings when you hear our favorite song or visit our favorite place?
31. Did you ever feel like I took our friendship for granted?
32. How do you remember our last conversation?
33. Was it difficult for you to move on?
34. Do you still think about our inside jokes?
35. Were there moments you felt proud of our bond?
36. Did you ever feel like we were growing in different directions?
37. How did our friendship impact your life?
38. What have you learned about yourself since we stopped talking?
39. Do you still cherish the gifts or mementos from our time together?
40. Have you spoken to others about our friendship ending?
41. Did you ever feel jealous or envious in our friendship?
42. How did you manage the days immediately after our fallout?
43. Were you hopeful that we might reconnect?
44. How did our friendship shape your views on trust and loyalty?
45. Were there times you felt we were drifting but didn’t know how to address it?
46. Did you ever feel like I wasn’t there for you when you needed it?
47. Have you forgiven both me and yourself for how things unfolded?
48. Were you ever scared of losing our bond?
49. How do you want to remember our friendship?
50. Do you ever wish we could start over?

About Past Disagreements

1. Can you recall the first disagreement we ever had?
2. How did you feel during our biggest argument?
3. Do you think our disagreements were often about the same core issue?
4. Was there ever a time when you felt I was being unreasonable?
5. Were there things you wished you had said differently during our disagreements?
6. Do you think we communicated effectively during our conflicts?
7. How did our disagreements affect your perspective on our friendship?
8. Were there times you felt I didn’t understand your point of view?
9. Do you believe I ever jumped to conclusions without hearing you out?
10. Was there a particular argument that stayed with you longer than others?
11. How did you cope after our disagreements?
12. Were there disagreements that you think we could’ve avoided?
13. Did our arguments ever change your feelings about our friendship?
14. Do you think pride got in the way of resolving our conflicts?
15. Were there moments you felt like I wasn’t listening during a disagreement?
16. How did you perceive my reactions during our arguments?
17. Do you think there were underlying issues we never addressed?
18. Were there any apologies you felt were left unsaid?
19. How did you feel when we couldn’t find a resolution?
20. Did our disagreements ever make you reconsider our bond?
21. Were there times you wished we had a mediator or someone to guide us through a disagreement?
22. How did you process our disagreements afterward?
23. Were there topics or subjects you felt we always clashed on?
24. Did you feel like I ever held grudges after arguments?
25. How did our disagreements affect your trust in me?
26. Were there things you felt I was particularly sensitive about?
27. Did you ever feel like our disagreements were one-sided?
28. How do you think we could have handled our disagreements better?
29. Was there ever an argument you regretted starting?
30. Did you ever feel like I misunderstood your intentions during a disagreement?
31. Were there times you wanted to reach out after an argument but hesitated?
32. Do you think our disagreements were more about the issue or how we felt about each other?
33. How did you view my approach to conflict resolution?
34. Were there disagreements that you felt ended prematurely?
35. Did you feel like our arguments were repetitive?
36. Were there any silent treatments after disagreements? How did you feel about them?
37. Did our disagreements ever impact how you interacted with mutual friends?
38. Were there times when you felt we were both saying the same thing, but in different ways?
39. Do you think external factors (like stress) played a role in our disagreements?
40. How do you reflect on our disagreements now that time has passed?

About Healing Old Wounds

1. How have you been healing since we stopped talking?
2. Have you found closure about our past?
3. What helped you move on from our friendship ending?
4. Do you think time has made it easier to cope?
5. Are there still things that hurt when you think about us?
6. Have you talked to anyone about how to heal?
7. What was the hardest part to get over?
8. Do you feel like you’ve forgiven me for past mistakes?
9. Have you forgiven yourself?
10. Are there things you wish you could fix?
11. Was there a moment you felt like you were starting to heal?
12. Did making new friends help you heal?
13. What would you say was our biggest wound?
14. Is there something that could make that wound heal faster?
15. Do you think talking about it now could help both of us heal?
16. Did you ever write down your feelings to help cope?
17. Are there places or songs you avoid because they remind you of us?
18. Do you feel like you’ve grown from the experience?
19. What advice would you give to someone trying to heal from a broken friendship?
20. Are there questions you’ve wanted to ask me that might help you find closure?
21. Was it hard for you to trust people again?
22. What’s something positive that came out of us parting ways?
23. Have you become better at handling disagreements?
24. Do you think healing is a process or a one-time event?
25. How do you wish I had handled the situation?
26. Do you still have hopes for us to mend things one day?
27. Have you replaced old habits we had together with new ones?
28. What’s the best way for us to respect each other’s healing process?
29. Do you still think about reaching out?
30. What do you think is the key to completely healing old wounds?

About Shared Memories

1. Do you remember the first day we met?
2. What’s your favorite memory of us together?
3. Do you still think about our road trips?
4. Remember that time we couldn’t stop laughing? What were we laughing about?
5. Which birthday of yours or mine stands out the most?
6. Do you still have those photos we took on our beach day?
7. Do you remember our late-night talks?
8. Which movie did we watch over and over again?
9. Have you been to our favorite cafe recently?
10. Remember when we tried cooking together? How did it turn out?
11. Do you still listen to the songs we loved?
12. What about the festivals or concerts we attended?
13. Remember that inside joke we always laughed about?
14. Have you been back to that park where we used to hang out?
15. Do you recall our rainy day adventures?
16. What was the book or story we both loved?
17. Do you remember the games we used to play?
18. Which holiday season was the most memorable for us?
19. Have you kept the gifts I gave you?
20. Remember the challenges or dares we took on?
21. Do you think about our shared celebrations and achievements?
22. What was the most adventurous thing we did together?
23. Remember our themed dress-up days?
24. Have you revisited any places we used to love?
25. Do you still eat our favorite shared snack?
26. What about the crafts or DIY projects we did together?
27. Remember our shared dreams and plans for the future?
28. Have you used the catchphrases we invented?
29. Do you remember the pets we adored?
30. What about the people we used to hang out with?
31. Have you ever recreated a memory we shared, but with someone else?
32. Do you recall the times we helped each other through tough spots?
33. Remember when we stayed up all night talking?
34. Do you still wear the matching outfits or accessories we bought?
35. What was the funniest mistake we ever made together?
36. Do you remember the songs we used to sing or dance to?
37. What was our most memorable trip or vacation?
38. Remember when we wrote or drew things for each other?
39. Have you kept any mementos from our time together?
40. Do you ever share stories about us with others?

About How They’ve Changed

1. How have you been since we last talked?
2. Have you picked up any new hobbies?
3. Do you still like the same music and movies?
4. Have your dreams or goals shifted in any way?
5. Did you move or change jobs?
6. Have you made new friends?
7. What’s the biggest lesson you’ve learned recently?
8. Are there things you see differently now?
9. How has your style or fashion sense evolved?
10. Do you still visit our old hangout spots?
11. What’s the latest book or story that inspired you?
12. Have you traveled to new places?
13. How have your tastes in food changed?
14. Do you still follow the same routines?
15. What’s the most exciting thing you’ve done lately?
16. Have you joined any groups or clubs?
17. How have you grown as a person?
18. Are there beliefs or values you see differently now?
19. Have you faced challenges that changed your perspective?
20. What’s a new skill you’ve learned?
21. Do you still celebrate the same traditions?
22. Have you discovered any new passions?
23. How has your outlook on relationships changed?
24. What are the recent milestones in your life?
25. Have you set new personal or career goals?
26. Are there new activities or events you participate in now?
27. How have you changed in how you handle disagreements?
28. Have you developed new habits that you’re proud of?
29. Do you have a new favorite place to relax or unwind?
30. How do you view our past in light of who you’ve become?

About Mutual Friends

1. How’s [mutual friend’s name] doing lately?
2. Do you still hang out with [mutual friend’s name]?
3. Has [mutual friend’s name] mentioned me to you recently?
4. How was the party/get-together with our group?
5. Did [mutual friend’s name] ever finish that project they were talking about?
6. Are you and [mutual friend’s name] still as close as before?
7. How was [mutual friend’s name]’s recent birthday celebration?
8. Do you guys still meet up at our old hangout spot?
9. How did [mutual friend’s name]’s trip go?
10. Are there any new friends in the group?
11. Did you and the group celebrate any recent milestones together?
12. How was [mutual friend’s name]’s new job or university experience?
13. Do you all still have those group chats?
14. How was the holiday gathering with everyone?
15. Did [mutual friend’s name] ever share their news with the group?
16. Are there any upcoming plans or get-togethers?
17. How’s [mutual friend’s name] coping after their recent challenge or setback?
18. Do you guys still share the same inside jokes?
19. Are there any events or festivals you all went to recently?
20. Has [mutual friend’s name] moved or traveled anywhere?
21. Do you and the group ever reminisce about old times?
22. How was the reunion or gathering with [mutual friend’s name]?
23. Did the group ever visit our favorite place again?
24. How’s [mutual friend’s name]’s family doing?
25. Are there any new stories or adventures you all shared?
26. Do you and [mutual friend’s name] still share the same hobbies or interests?
27. How was the last outing or trip with the group?
28. Did [mutual friend’s name] ever mention our time together?
29. How’s everyone from the group doing in general?
30. Have there been any big changes or news among our mutual friends?

About Lessons Learned

1. What’s the biggest lesson you’ve learned since we parted ways?
2. Do you feel our friendship taught you something about trust?
3. How have you learned to handle disagreements differently?
4. Did our time together change how you approach new friendships?
5. What lessons did you learn about communication from us?
6. Has our history influenced your personal boundaries in any way?
7. How have you learned to prioritize friendships?
8. Did our experience teach you anything about forgiveness?
9. Have you learned more about your own strengths and weaknesses?
10. How has our friendship influenced your understanding of loyalty?
11. Did our moments together teach you about the value of time?
12. What did you learn about handling tough times from our experiences?
13. Have you found ways to prevent misunderstandings in relationships?
14. How has our friendship shaped your views on commitment in friendships?
15. Did we teach each other about the importance of patience?
16. What lessons on self-awareness did you gather from our time?
17. How have you learned to set and respect boundaries better?
18. Did our journey teach you about the significance of mutual respect?
19. What have you learned about your own emotional needs?
20. How have you changed in how you express and manage feelings?
21. Have you learned any lessons about when to hold on and when to let go?
22. Did our friendship influence how you see change and growth in relationships?
23. How has our story taught you about the value of memories?
24. Have you learned more about your personal values and principles?
25. Did we teach each other about the importance of understanding?
26. How has our history influenced your perspective on closure?
27. Did our time together offer any insights about compatibility in friendships?
28. Have you reflected on how to be a better listener?
29. What did you learn about personal space and freedom in friendships?
30. How have our shared experiences shaped your views on reconciliation?

About Rebuilding Trust

1. Do you think trust between us can be rebuilt?
2. What would be the first step in rebuilding trust for you?
3. Are there specific actions that broke your trust in me?
4. What can I do to start earning your trust back?
5. Is there a time frame you have in mind for rebuilding trust?
6. Would open communication help mend trust between us?
7. Are there boundaries that need to be set for trust to be rebuilt?
8. Would you be open to a fresh start?
9. How important is trust to you in a friendship?
10. What are some trust breakers you think we should avoid?
11. Would an apology make a difference in how you see the situation?
12. What do you believe are the foundations for trust?
13. How can we handle disagreements better to maintain trust?
14. Are there past issues we need to resolve to rebuild trust?
15. Do actions or words hold more weight for you in trusting someone again?
16. Is there anything you think I don’t understand about why trust was broken?
17. How can we check in with each other to ensure trust is being rebuilt?
18. What are some signs for you that trust is being restored?
19. Would discussing it with a mediator or counselor help?
20. Do you believe trust is something that can be repaired over time?
21. What would be a deal-breaker for you in this process?
22. How can we be more transparent with each other?
23. Are there any assurances or commitments you’d like to see?
24. Can trust be partial, or is it an all-or-nothing for you?
25. What are your expectations in a friendship where trust is strong?
26. Is rebuilding trust a joint effort, or is it more on one person?
27. Are there trust exercises or activities you think would help?
28. What does accountability look like for you in rebuilding trust?
29. Would setting mutual goals help in rebuilding trust?
30. How will we know when trust is fully restored between us?

About Their Current Life

1. How have you been lately?
2. Are you working or studying somewhere new?
3. Have you taken up any new hobbies?
4. How’s your family doing?
5. Have you made new friends or met interesting people?
6. Are you still living in the same place?
7. Have you traveled or gone on any trips recently?
8. What’s your favorite thing to do these days?
9. Have you watched any good movies or shows lately?
10. How do you usually spend your weekends?
11. Have you attended any fun events or festivals?
12. What’s the latest book you’ve read?
13. How do you unwind or relax after a long day?
14. Are you still into [specific interest or hobby you knew they had]?
15. Have you tried any new foods or restaurants?
16. Are there new music or artists you’re into?
17. How do you stay active or fit?
18. Have you visited any cool places in town?
19. Do you have any upcoming plans or vacations?
20. How’s your current job or course going?
21. Have you taken on any new challenges or projects?
22. Are there any causes or charities you’re involved with now?
23. How do you usually celebrate special occasions?
24. Have you picked up any new skills?
25. What’s something you’re really proud of recently?
26. How do you spend your free time these days?
27. Have you had any memorable experiences lately?
28. Are there any new goals or dreams you’re working towards?
29. How’s your day-to-day routine like now?
30. What’s something exciting you’re looking forward to?

About Future Plans

1. What are your goals for the upcoming year?
2. Do you have any travel plans lined up?
3. Are you thinking about trying a new job or career path?
4. Do you plan on moving to a new place anytime soon?
5. Are there new hobbies or activities you want to explore?
6. Do you have any big events or milestones coming up?
7. Are you planning to go back to school or take any courses?
8. What’s on your bucket list for the next few years?
9. Are there personal goals you’re working towards?
10. Do you have any plans to reconnect with old friends or family?
11. Are there places you’ve always wanted to visit?
12. Do you see yourself settling down or starting a family in the future?
13. Are there new skills or languages you want to learn?
14. Do you have any financial or investment goals?
15. Are you considering any major life changes?
16. How do you envision your life five years from now?
17. Are there any books or courses you’re planning to dive into?
18. Do you have plans to attend any concerts or festivals?
19. Are you thinking about adopting a pet in the future?
20. Is there a dream project or endeavor you want to pursue?
21. Are you planning to explore any new fitness or wellness routines?
22. Do you have aspirations to write, paint, or create something?
23. Are there any volunteer or charity projects you’re looking at?
24. Do you foresee any changes in your social or personal life?
25. What kind of adventures or experiences are you hoping for?
26. Are there any resolutions or promises you’ve made to yourself?
27. How do you plan to grow personally and professionally?
28. Are there specific people you want to meet or work with?
29. Do you have a vision or dream place where you’d like to live?
30. What are the biggest hopes you have for your future?

Frequently Asked Questions

How can I ensure the conversation remains positive and constructive?

Focus on:

• Active listening without interrupting.
• Avoiding blame or accusatory language.
• Using “I” statements to express feelings.
• Seeking understanding rather than “winning” the conversation.

Is there any merit in involving a mutual friend in our conversation?

Involving a mutual friend can provide a neutral perspective, but it’s crucial to ensure both you and your ex-best friend are comfortable with this. It’s also vital that the mutual friend remains unbiased.