70 Questions to Ask Your Ex Boyfriend

Breaking up is tough, and sometimes the hardest part is knowing what to say when you’re face-to-face with your ex.

It’s totally normal to have lingering questions that need answers before you can fully move on.

I’ll walk you through some thoughtful, gentle questions that can help you get the clarity you’re looking for.

These questions are here to guide you through the tough conversations, help you heal, and maybe even give you a fresh perspective on your past relationship.

Understanding the Breakup

  1. What do you think went wrong between us?
  2. Was there a specific moment when you knew it was over?
  3. Did you ever feel like I wasn’t meeting your needs in the relationship?
  4. Were there things I did that pushed you away?
  5. How long were you thinking about breaking up before it happened?
  6. Do you think we grew apart over time, or was it something specific that caused the breakup?
  7. Were there times you felt unheard or misunderstood by me?
  8. Did our different life goals contribute to the breakup?
  9. Do you feel like we gave our relationship enough time to work?
  10. What could I have done differently?

Gaining Closure

  1. Do you feel there are any apologies needed from either side?
  2. Is there anything you regret saying or doing?
  3. Is there something you would like me to know as you move forward?
  4. Can we leave things on a positive note today?
  5. Is there anything you wish you could have told me before we ended things?
  6. How do you feel about the way we ended things?
  7. Do you think we could have handled the breakup differently?
  8. Was there something I did that made it harder for you to move on?
  9. Is there a part of our relationship that you still think about?
  10. Looking back, do you think our breakup was inevitable?

Emotional Healing

  1. How did you handle the emotional aftermath of our breakup?
  2. Did you ever feel anger or resentment toward me after we ended things?
  3. Were there any specific memories that were hard for you to let go of?
  4. What did you learn about yourself from our relationship?
  5. Did you find yourself comparing new relationships to what we had?
  6. Were there moments when you questioned if you made the right decision?
  7. How did you handle seeing things that reminded you of our relationship?
  8. Have you been able to forgive yourself and me for our past mistakes?
  9. Were there any habits or routines you changed to help you move on?
  10. Did you find it difficult to open up to others after we broke up?

Gaining Perspective

  1. Do you think we both grew as individuals from our time together?
  2. How do you think our relationship shaped who you are today?
  3. Do you think we brought out the best in each other?
  4. Looking back, do you think we were compatible as a couple?
  5. What were some of the happiest moments we shared together?
  6. Do you think we could have worked out if we had met at a different time in our lives?
  7. Do you think our relationship helped you grow emotionally?
  8. Looking back, do you think we were on the same page about our future together?
  9. How have your priorities in a relationship changed after being with me?
  10. What do you think was missing in our understanding of each other?

Current Feelings

  1. How do you currently feel about me?
  2. Do you feel indifferent towards me now, or do you still have strong feelings?
  3. How comfortable are you with maintaining a friendship?
  4. Are there feelings of resentment or anger you still hold?
  5. What emotions come up for you when you see me or hear about me?
  6. Do you have any regrets when you think about us?
  7. How does reflecting on our relationship make you feel today?
  8. Do you ever wish things had ended differently between us?
  9. Do you ever wonder what it would be like if we were still together?
  10. Are there any regrets you have about how you treated me?

Moving Forward

  1. Do you think we can be friends now that we’ve had time apart?
  2. How do you see us interacting in the future, if at all?
  3. Do you think we need to set boundaries to move forward?
  4. What kind of relationship do you think we could have now, if any?
  5. Do you think it’s better for us to have a clean break or stay connected in some way?
  6. How do you feel about us possibly working together in the future?
  7. Do you think we’ll be able to look back on our relationship positively in the future?
  8. What changes have you made in your life since our breakup?
  9. What are you most looking forward to right now?
  10. What personal improvements are you focusing on?

Rekindling the Relationship

  1. Have you ever thought about getting back together?
  2. Do you think we’re better suited now than we were before?
  3. What would be your main goal if we were to start over?
  4. How do you think we can avoid past mistakes if we decide to reconcile?
  5. What part of our relationship do you think would need the most attention if we were to reconnect?
  6. How do you think we could make our relationship stronger if we tried again?
  7. Do you think our past issues are something we can overcome if we try again?
  8. How would you handle things differently this time around?
  9. Do you think we’ve both grown enough to make it work this time?
  10. What would make you hesitant to get back together?

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Bea is an editor and writer with a passion for literature and self-improvement. Her ability to combine these two interests enables her to write informative and thought-provoking articles that positively impact society. She enjoys reading stories and listening to music in her spare time.