17 Questions I Asked My Ex About Our Breakup

Bruce Da Silva
10 min readJan 12, 2021


Summer 2016 day of the hike

I am borrowing this idea from “Scorpio Poetry”. Their idea was to reconnect with an ex and ask some personal questions that most would find uncomfortable but would be necessary to no longer live in ignorance and maybe even grow. I decided to ask a girlfriend of mine from college and was genuinely surprised she was game to take part.

I wanted to ask these questions to challenge myself to rethink a part of my past that I hadn’t actually fully thought about. I was nervous to ask some of the questions but glad that I did. Here it goes.

  1. What’s your biggest regret about our relationship?

I’ve never had any regrets in our relationship. There was never a point where I wish I said or did something differently. Our relationship was fun for me because I was going through a time of self discovery and so I was just myself to the fullest. I don’t think I was ever really nervous. Mostly when I do regret something I just wish, “why can’t you just channel your inner self? Why were you nervous here? Why were you not yourself here?” In relationships, especially with one’s I should never have been in. With us it was good because I was able to find part of myself where I was like “I like this girl.”

2. What’s your favorite memory of us being together?

I have to think about it. I feel like my favorite memory was in Lancaster after we had dinner and your sister went to bed and your friend stayed home and we went out and did whatever. I think we went into a hotel and sat there for a while. That was my favorite because it was still new. I remember you texted me randomly after we met at the last night in Florida. You were like, “hey, I’m going to my sister’s in Lancaster. Let’s meet up!” And I was like, “OK.” I think that was my favorite because it was new and it was still exciting. That whole day was just fun. Meeting your sister, going on a hike was fun, going out to dinner at the Indian place was so fun. That day was just my favorite because we were still fun and it was so new.

3. What’s your least favorite memory of me?

I think .. ohh.. OH! Actually, I don’t know. I think I would say the time when you fell. Because that was so scary. But, I also like, in that moment, when you were like losing it, I was like, praying. I was like, please help him. I knew that you were not okay. Obviously you weren’t ok. I was like, holy shit. Like, this is out of my control. I was just like please God help this kid. I don’t know what to do if some disaster were to happen right now. I can’t climb down this cliff or have a helicopter come pick his up. And you would probably not make it since it was a really bad cliff. That moment was just my least favorite because there was so much fear there but then also it was okay because you were okay in the end.

4. What would you have done differently?

That’s a hard question for me because I don’t think that way. I don’t think what would I have done differently. I guess I do in certain cases and certain relationships. For me, this one just was and then it wasn’t. It was good when it was and then I just needed to unwind and grow at the time that I did. I think if anything what I would have done differently was to spend more time together cause we were living in different states, you were in Brasil for a long time, and we connected through talking on the phone a lot or texting a lot but it wasn’t like.. it was still a relationship but it wasn’t, we weren’t together every other day. Maybe if we were things could have been different.

5. Do you still think about me?

I mean I do because you were a part of my life. Do I think about you in a romantic way still? No, because it’s been so long and we’ve both had so much life and other romances and stuff. I still see your posts and still appreciate your writings and what you do and where you’ve been and where you’ve gone after but I think of you in a way where I still acknowledge your presence with a good feeling, like it’s not bad it’s just there.

6. Do you wish we could work it out now?

No. I say that because everything is new for me in life and I keep evolving into new places and one thing that I promised myself is that I won’t regress anymore. I don’t think you would be a regression at all like I wouldn’t be moving backwards. If anything I would be moving forward because we have both grown so much. For me right now where I am at with going to school I just want to keep my focus right. I want it to take me to the place I am supposed to go. With the way things worked out they worked out for a reason.

7. Do you ever talk about me with your friends?

I think sometimes. I actually just got out of a relationship and I know I mentioned you once to him. It was silly and I was like “oh, that’s just Bruce.” But I forget why, I don’t know, I can’t think of it. It wasn’t anything bad. With one of my friends I sometimes bring you up for a second but it’s never like something to figure out. It’s not why did this or that happen but the flow of the conversation where it comes up.

8. Do any songs or TV shows remind you of me?

Frasier. I remember we watched it before. Also anything with Justin Bieber and John Mayer sometimes. The song called XX by Marc E. Bassy also.

9. What do you think of me now?

I think that you’re very interesting. I mean, you have done really interesting things. You were in the Peace Corps then went to school in Israel. I think it’s really cool what you’ve done and where you’ve been even though I don’t really know the stories but I know they happened. I think it’s really good that you explore things philosophically and you look for answers and truth and I appreciate that you have no ego at all.

10. Do you think you settled with our relationship?

No? No. I don’t think so. I settled with my own everyday doings and calling you after work. I think I did in a way where you were my comfort for a lot of things. If something was on my mind or whatever I was going through or a long day of work at the Hilton we would talk. I guess I settled in that and then just having you be my rock I guess. You were just there for me. I mean, I definitely settled into learning about your spontaneity. I was definitely allured by it. Not yearning for it but like you feel the yearning and then you go with it. You feel the yearning that you didn’t even know was yearning. I liked that. Whenever we were planning to go to the concerts I was apprehensive about it because of the money and travel and you were like, “let’s just do it, let’s do it, let’s do it.” Then I’m like “ok, let’s do it.” I settled into that feeling of being spontaneous which I feel like I carry with me now.

11. If you could tell me anything what would you say?

I would just say that.. I don’t want to say I’m proud of you cause that’s weird because that makes me feel.. like you’re not subordinate to me like I don’t feel that way but I am proud of you. I feel like with breakups that are hard on people you can either go one way or the other and I feel like you went bigger. You thought how can I expand on myself and learn. I don’t know what you went through personally but I know that you went off and did really great big things. That’s always good.

12. When we first got together did you want us to last or did you have an exit strategy ready to use?

No. I was like, “oh maybe this is why I am in Florida. Maybe I was supposed to meet this person.” No I didn’t have an exit strategy at all. To me it was like, “oh, this person matches my energy, is spontaneous, and fun.”

13. What do you miss about me the most?

I guess just having a person that is super validating since a lot of the time when you go through life on your own you don’t really know if you’re doing something good or something really wrong or something not in alignment for you and we were definitely friends as well as a relationship emotional type thing so I guess I just miss having that friend part. It was just confirming and validating.

14. Do you think we could ever be friends?

Yes. We should be friends. I feel like we have similar outlooks and ways of thinking about life.

15. Do you think we’re compatible?

I don’t know now because we’ve gone our separate ways and I feel like going through how old we were then and how old we are now those are huge years for growth and transformation. Right now I don’t know but then I feel we were in the beginning like in most relationships and then I feel like I started to drift more to go solo. I think we were compatible then but I think I was growing more and urging to grow more and not settle. I feel like we were compatible in the beginning for sure because we definitely could be in the same moment together and that’s important in a relationship and we weren’t operating from different universes or anything and we could stare at the same picture and understand where we were both coming from and that’s compatibility. I feel like that’s an innate quality. I don’t think that goes anywhere.

Wait, that wasn’t a good answer. That was so subjective…. it’s so hard for me to put words to things. Ok, ok. I think it’s good actually. Simply put, it has been so long so I don’t know. Maybe. Maybe you grew this much and I grew this much and I don’t know. Compatibility is so much more than where you are mentality. It’s body language and intimacy too.

16. How did you get over the breakup?

For me I wasn’t hurting after. For a while I felt bad that I wasn’t hurting because I felt I should have been. We were together for a while. What became apparent to me was how different we were. At first I thought we were so similar and that we were able to see things the same. After a while it became more apparent that we were so different. For me I understood the differences and when I found that I accepted it easily for some reason. Ok, we’re different and I’m going to go my own way. I’ve always found comfort in myself like I’ve always been my own person. I do best in life on my own. For me it was a new breath of finding my inner core again so it was good for me. I needed it. I get suffocated not in a bad way but for me after a while I just felt my own security in myself instead of trying to find it in another person. It was hard to go from talking everyday to not talking to them anymore. I feel that change was calling me to go my own way like it usually does.

It wasn’t in a bad way. I don’t want you to think I was dying on the inside. It was more freeing for me to be secluded and isolated. Whenever I get into relationships I always put all of me into that person and I try to dish out the best parts of me for them to see and be validated. I realized that I was giving all of me and I do this with everybody. I give all of me and then I become one with them. Then my individuality I lose it. Then it’s hard because at times I’ll get little messages and confirmations telling me to break off and let go. It was more just a new start so I wasn’t hurting and I didn’t need to get through it or anything but I more so had to look at it in a way that it wasn’t bad and that it’s oaky to have people in your life that come in and make an impact and then you go your separate ways because that’s how it goes.

17. Would you do it all over again the exact same way?

Yeah! That’s an easy one. That’s a weird question though. It was just a sign of the times and where we were and what happened. Would I want to live through it again? Probably not since I lived so much through that time and I don’t want to live it over again. I wouldn’t want it to be erased. I mean I wouldn’t do it all over again because why would you do anything over again? Everything has a place and time and reason and if I had to do it all over again I would just forget everything I learned and expanded from and I wouldn’t want that. I’m glad it happened and glad it was there.

I mean I wouldn’t change it. I’m glad it happened. I would wanna relive the parts that were exciting because they were exciting but I wouldn’t want to relive the parts that weren’t. I’m just accepting of how it happened, why it happened.

I was truly unsure of the answers I would get and was surprised to hear some of them. Going through this helped me to understand the other person’s experience through our relationship and see how they view the experience in hindsight. It was fun to catch up with her and it didn’t even seem like we missed a beat. As she said, I think we both grew and matured in ways that we probably wouldn’t recognize the two of us from four years ago. That’s how long it’s been since we actually even spoke face to face! Just wild.

All in all, this exercise is great to use when trying to self reflect and understand past relationships one may have been in. Regardless if one is trying to fix, recreate, or simply understand their past relationship with an ex, the benefit of this exercise is to make peace with our past and better prepare for the next special relationship we find ourselves in.

I hope you will give it a try.



Bruce Da Silva

28-year-young Brasilian-American life coach and philosopher living in LA on a journey of discovery and hunger for knowledge in all capacities. Welcome 💭