Some breakups aren't an even split. They can feel as if they came out of nowhere or as if one partner wants it more than the other. But there's always a lesson in them.
The internet was reminded of this when u/FwhatYoulike asked men, "What's your biggest regret from a failed relationship?" There were many cathartic responses, so here are some of the ones that stood out:
1. "I regret pushing someone away because I was overwhelmed at work and I didn't want them to see the 'bad' side of me. I've never gotten along with someone the way I did with her. From the moment we met, it was perfect, and I just threw it away."
2. "Feeling like I wasted her time. We broke it off because I was on the fence about wanting kids and she absolutely wanted them. I was 29 and she was 30. Now that it's been a couple of years since we broke up, I think that we both spent so much time single and feeling like we were never going to find our person that neither of us wanted to confront a major deal breaker. So stupid. After lots of crying and couples therapy sessions, we broke it off. I really hope she finds her person and she gets the family she has always wanted."
"We were great together. I eventually got pressed really hard at the two-year mark and was forced to think on it. Prior to this, I never really thought about kids; kinda just figured it would happen if it was meant to. Now I know I don't want them."
3. "I was a complete fucking idiot during the breakup process. I was wrong about my feelings, and I thought she was the woman of my life. But my feelings were not about her. They were about the mental image I had of her. I idealized her in every aspect because I had a poor image of myself. After being miserable for a couple of months, I started seeing a therapist, and it helped me tremendously in getting over her."
4. "One of my exes took me to see Twilight. She was a huge fan. I cracked jokes throughout and criticized the film. Now I can see clearly how I fucked up. She knew I had no interest in those films, but she wanted to use it as a chance to bond with me. I should've focused on her, not the movie. She was in a romantic mood, and I absolutely killed it. If I could go back and do it again, I would have her resting on my chest, silently watching the movie, maybe give her the occasional kiss on the forehead, and ask a few questions about the characters in the movie. I wish that I made her feel as though her interests and feelings were important to me. I missed a powerful opportunity to bond with my girlfriend and instead just pouted the whole time."
5. "I betrayed her trust. I didn't listen, learn, or grow enough to deserve her. She communicated what her needs were, and instead of trusting her, I let my fears, insecurities, and impulses drive dishonest behavior. Even though I now know more about why I'm this way and am seeking to improve, it all seems really empty right now."
6. "When I was younger, I'd just drop them once I got bored. Now I wish I'd been kinder. I wasn't mean, just indifferent."
7. "I regret not standing up for myself and my values sooner, and instead trying to change myself for the sake of the relationship, which ending up failing anyway. I started putting my own hobbies aside to be there for her all of the time. I didn't realize until much later that I was putting my own life on standby to be with her. I never complained about some of the out-of-line things she said to me, because I'm a pleaser at heart. I just closed my eyes and hoped for the best to try to make the miracle happen, and forgot myself along the way."
8. "I regret cheating. Not so much from losing the relationship but because I hurt her so bad with my betrayal. She didn't deserve what I did. She was rightly pissed and basically cut off contact with me, so there was little, if any, closure. I'm still dragging that baggage around to this day myself, and I hope she isn't too."
9. "I was violent at times. I was 15 years old when I ended up with a girl way out of my league. We stayed together until we were 20, and I treated her terribly. There were no punches or kicks, but I did push and pull her, and that's just as bad, in my eyes. I was ashamed of my behavior, even when doing it, and I wanted to ensure that I never acted that way again, so I started going to counseling. As a result of that relationship, I've been up front and honest in any relationship that has become serious so that they know about my past. I can safely say that for 22 years, I've never gone near being that person again."
10. "When I was 16, I went to Boston for a hockey tournament. I am from Canada and had never been to that area before. I was so excited to see such a historical place in US history. We got the whole tour of Harvard, and I got this unbelievable Harvard hoodie. I left the hoodie at her place, and after the breakup, I never saw it again. I’m now 25 years old and I still wish I had that hoodie."
11. "Not telling her that long distance sucked as much as it did. She always felt bad about us being in that situation, so I tried to be as cool and accepting about it as possible for her sake. In hindsight, I think she just thought I didn't care."
12. "Not leaving earlier when seeing so many mental health issues and red flags from her past."
13. "I regret not keeping in contact. I was forced to break up with him, and I ended up marrying a woman a year later — he didn't know I was bisexual. He had to find out from a mutual acquaintance, and it broke his heart even more than I already had. I should have told him what was going on myself."
14. "I didn’t stick it out. The going got rough for a little because of my stress and anxiety, so I bailed thinking it would make me happier. It didn't. That was three months ago, and I'm still trying to fix what I’ve done."
15. "That I forgave her after she cheated on me the first time, and wasted another four years of my life with her. And of course, she cheated again. I could have had a much better life if I didn't have her weighing me down emotionally."
16. "So many times I kept things to myself because I was afraid of her reaction. It resulted in me either not setting proper boundaries or silently resenting her for something she wasn't even aware of. So dumb. I ruined more than one relationship with this. The funny thing is, once I stopped being afraid of the response, the conversations were never as bad as they were in my mind."
17. "Trying to explain myself to someone who didn't care. Everything this person said about me was wrong, but I realized they just ultimately wanted to end things. I learned that once someone has made up their mind about you, even if it's wrong, don't try to change their mind. Just walk away and say it was fun."
18. "She was from another country on an exchange program and told me straight up to say the word and she’d stay. Being 23 years old at the time and not having my life sorted out played a big part in me telling her no. I regret that. For all I know, it may not have worked out, but not even trying still bothers me quite a bit. We promised each other we’d try to stay friends after she left, but things got awkward, and arguments often happened. Both of us admitted to each other that the 'what if' sentiment was why the arguments happened, and those feelings never fully went away. So we decided to cut ties."
"It sucked, but it was for the best."
19. "I regret starting it at all, to be honest. I loved her, but we were both in a bad place and not compatible at all. Neither of us should have been in a relationship at all at that stage of our lives. I had a drinking problem at that time, and while it didn't make me abusive or anything, it did sure make me sloppy. I was kind of a mess. I cringe at my old pictures. I really did look like a disaster. I had no self-love, and she could feel it. Because of the drinking, I was underemployed and often broke. My energy was low and my health was bad. I had a problem with lifelong depression that I had been neglecting. There wasn't any future with me. I've been sober for four years now, and it's been seven years since we broke up. I absolutely loved her, and it feels both like it never happened and also like it happened last month. It's one of my biggest regrets."
20. "Not giving the same amount of effort. I had a really good girlfriend who went way beyond for me, and my lack of effort and selfishness got in the way. Once she was gone, I realized what I truly lost, and how special and great she was. I even tried reaching out to her, but she wanted nothing to do with me. The experience helped me grow and become more mature in my relationships, so honestly, I feel like I needed this experience or else I would've continued being the same piece of shit."
21. "Not being mature enough to stay faithful. I grew up a really skinny, tall, awkward kid with somewhat low self-esteem. I didn't really get confident until around 19 years old when I finished basic training. I put on some muscle and started getting more attention from women and used that to boost my ego. In my early 20s, I met a beautiful, great woman who loved and cared about me. I broke her heart because I wasn't ready to be a one-woman man. I had an older ex who also just happened to be one of the finest women I had ever been with, but she was toxic and liked to play games. I saw her out one night and went home with her. That ex sent my then-girlfriend a picture of me sleeping on Facebook for no other reason than to break us up. She didn't deserve that, and it was totally my fault for giving in to temptation."
22. "I gave up a great woman because I wanted to hold out hope for someone else who never really gave a shit about me in the first place. I treated the nice woman like crap, not really being as available as I could have been, and putting her on the back burner."
"I actually got to apologize years later, and she said she totally understood and forgave me. I still felt silly, though."
23. "Being insecure and jealous toward her because I was cheated on in a past relationship. I was accusing her of cheating constantly, even though deep down, I knew she would never do that to me. I had abandonment and mental health issues that I never got help for, and that finally drove her away. She stayed way longer than most women would have, and the regret and guilt I have never goes away."
24. "Honestly, I regret ever meeting her. She was cheating on me after three years. On my birthday. She was sexting another guy while spending time with me. I invested everything into her, thinking she was doing the same with me. Turns out, when it went too long without her getting what she wanted, she just threw everything away."
25. "I never told my ex-girlfriend’s parents how much I loved and appreciated them for always making me feel welcome in their home, all the times they fed me, and overall how nice they were to me. They literally gave me a key to their house. I would always do things to show my appreciation throughout the relationship, but looking back, I should’ve given them more of a legitimate goodbye once I knew things were over. They watched me grow as a man from age 19 to 26, and the way I just disappeared after their daughter broke up with me out of nowhere was straight-up bullshit. I owed them more than that. That’s the biggest regret from the relationship."
26. "That I let her keep the dog."
27. "Letting it completely destroy my self-esteem and self-worth. I had a girlfriend between the extremely formative years of 13 and 17. I was told by many that she was way out of my league, and I guess we were at an age where she couldn’t see that. I started to understand that as we got older, and I became more jealous and a little controlling. She broke it off and started dating the guy I always wondered if she secretly liked. She had sex with him a month into their relationship, while we never did once in our four and a half years together. Completely broke me for years."
"I am 30 now, have a fiancé, and am happier than I’ve ever been. But when I look at my life, that breakup still had the biggest single-event impact on my entire life."
28. "I wasted 18 months in couples therapy with my ex before we finally decided to throw in the towel on our marriage. Reflecting on that helped me realize I am loyal to a fault and that I need to learn to let go sooner. I had myself convinced that if I just didn't stop trying, I could make it work. I was wrong but wouldn't let myself believe that until it was finally over. It's been a couple of years now, and I see the mistakes and how foolish I was, but love does strange things to the mind. I missed a lot of personal growth and let my career fall by the wayside in order to fight for someone who wasn't fighting for me. But it taught me to value myself more and to stand up for my ideals and my well-being. So I don't hold a grudge."
29. "I had an emotional affair. I didn't know what the hell was going on until it was too late. I confessed, broke up with her, and immediately knew I'd made a mistake. I begged for forgiveness, and she came back. Unfortunately, I just pushed past it and never fully addressed it. Four years later, after we married, she left out of the blue, saying she couldn't get past the hurt I caused. It was the biggest regret of my life, and I lost the love of my life for it."
30. "Wishing I actually did better listening to what was really on her mind, and articulating my thoughts more effectively. I think, really, the breakdown began when effective communication in general between us started to fall off. Toward the end, it was a lot more fights, some of which were pointless and some that were justifiable. But some of it could also have been avoided if I did my part in communicating better with her."
31. "My biggest regret is how toxic I was in most of my relationships. I've read a lot about manipulative behavior, narcissism, gaslighting, and general asshole behavior. I did some research into these behaviors and realized that I was an asshole in most of my relationships. I've been to a therapist, worked on cognitive behavioral thinking, and reflected a lot on what I needed to do to become a better person. I'm 10 years into a marriage that has its ups and downs, but I put in the work every day not to repeat my prior behavior patterns."
Which responses resonated with you? And if you'd like to share, what's your own biggest regret from a past relationship? Let me know in the comments.
Note: Some responses have been edited for length and/or clarity.