Exes Share Why They Regret Breaking Up With Their Partners

November 13, 2018 | Miles Brucker

Exes Share Why They Regret Breaking Up With Their Partners

We all make mistakes from time to time. However, there is hardly a kind of mistake more painful and heartbreaking than one that costs us the love of our life.

Getting over a breakup is extremely hard to begin with, but when it’s one that we ourselves caused, it’s on a whole other level–as anyone who’s been through this sad scenario knows all too well.

Here are 40 heartbreaking stories of exes who regret ending their relationships.

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40. Regrets, I've Had a Few

I broke up with my partner not long ago, but I'm not exactly sure about my decision, even though it was something I contemplated for some time. It seems like we tend to reminisce on the good things and maybe over-romanticize the past and how things were. Thinking back on the actual problems we had, however, I can recall why things went that way. In that sense, my best answer is that the "oh no" feeling comes and goes from time to time, and I think that's natural. In other words, sometimes even if you think you made the right decision, it’s hard not to have at least some level of regretful feelings about someone you once cared about.

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38. It May Be Painful, But You Probably Made a Good Choice

My biggest regret is thinking that no matter how much I changed for him, I knew in the back of my head that it would never be enough. I knew that in the end he would never fully love me. And that his love was full of conditions. That hurt me the most—the pain I put myself through. I should've let it go months before I did. I wish so badly I didn't go through that because now I have such a hard time believing I'm worthy of love just the way I am. And somehow, through all of this, I still wish I was with him a lot of the time.

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36. You’ll Never Live It Down

I dated a girl for almost two years as a 15-year-old. I started to wonder what dating other girls was like, so I broke it up so we could date other people.

I regret it because I eventually married her and she now brings it up routinely.

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35. Why Can’t We See Things For What They Are?

I dated around and all men were awful. They were just horrible. And here I’d left the best person I knew. I don’t know how it could have worked out any other way, but I’ve regretted it for almost ten years now. He was the love of my life. And now he has a different wife and a kid. I think about him every day. I was such an idiot. He won’t even talk to me anymore.

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34. People Should Mind Their Own Business

We tried doing long distance for longer than we'd actually been together in person. I didn't know how hard that would be and ended up breaking it off because I thought that me being attracted to other people was a bad sign. It didn't help that there was a guy seriously preying on my insecurities and telling me I would probably break up with him anyway only because he was trying to get with me. I have regretted it every day once my muddled mind woke up.

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33. Hopefully This Time Will Be Different!

I broke up with my eighth-grade boyfriend. Regretted it later when I realized how amazing and good-looking he really was. We kept in contact through social media but didn't speak much after. Flash forward ten years, I was back in my hometown and was honestly just looking for a hookup before heading back home. Ended up being the best date ever, we started dating shortly after and now live together.

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32. Goodness Is a Rare Commodity

My mom left my step dad and he got remarried to a great lady and is super happy now. My mom told me recently that leaving him was the biggest mistake she ever made because he was the only good man she ever really knew. We all have Christmas at their house every year, but my poor mom has to watch them being happy together every year while she lives alone.

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31. Lessons Learned

I dumped somebody because we reached that serious stage and I didn't, at the time, want to deal with the extra maintenance, especially as she was high maintenance to begin with. Hugely regretted it instantly. I now make dating decisions based entirely on compatibility. This has made all the mind traffic you get from dating so much easier to handle.

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30. So... You Regret It Because He Was Nice, or Because He Got Rich?

Back in freshman year of high school, I dumped this guy who had been nothing but nice to me for a guy who treated me like garbage and played around. The guy I dumped got a new girlfriend not long after, and they've been dating ever since. He turned out to be the class valedictorian, got into an Ivy League college, and was hired by a multinational company. So, that was that, I guess.

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29. The Grass is Always Greener on the Other Side

My friend dumped his girlfriend of 12 years because he'd never dated anyone but her, they were struggling financially, and he wanted the chance to experience more relationships. Right after the breakup, she finished her PhD and started making six figures. She found someone else and got married within a year.

My friend tried dating a couple of people, but none of them have worked out and he still misses her. He said the moment he realized that he made a huge mistake was when he saw her wedding photos on Facebook and started crying.

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28. I Hope You Solve Your Problems Some Day

I pushed her away because I got overwhelmed. I miss her.

I have this habit in relationships where I always end things whenever I feel overwhelmed. I really, really loved her. But little things start to pile up. I don’t say how I feel because I just don’t like confrontation. And then one day I just didn’t love her like I used to. I don’t know why.

I fell out and ended it. She tried so hard to figure things out with us, but it just... I didn’t want to try. It didn’t seem fair to her to continue this when I’m just going to keep feeling suffocated. And when she tried to help, I felt trapped.

I don’t know why I’m like this. And I know she really cared and loved me. Part of me wants to reach out to her again and really try to mend things, and figure out how to not feel so suffocated anymore. I don’t think it’s anything she did, she was really understanding... it’s just me. I don’t know how to deal with me. And I miss her.

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27. Waiting It out

I don't know if I should have broken up with him. He makes me happy. I don't think I will ever find a guy as good as him. I think I will regret it because I won't find another guy like him. Loyal, hardworking, doesn't need to look at or fantasize about other women, same goals for the future, weird, smart, funny.

We have different cultures though. He is Indian. I was told his family would never be a problem on this front. After three years, I wanted to move in together because he was moving away for a job. His parents said no because they want us to have our careers established. He risks being disowned apparently if he goes against their wishes. We both want to go into the medical field, so that could take years to become established, and I'm sick of seeing my boyfriend of three years only once a week. When he moves away, that will become once a month if we are lucky. I love him but I need more affection, once a week isn't enough. Texting isn't enough. So I ended it. But I'm constantly filled with so much regret and sadness.

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26. You Can’t Drink Your Troubles Away Forever

I ruined my relationship with my college boyfriend because of my alcoholism. It had really just started at that time and I didn’t even know how bad it already got. I was nuts drunk and he put it up with so much. Honestly, I had the “oh no” moment soon after. He was the nicest guy ever and he loved me so much. He was so smart and goofy and just a real catch and, last I’ve heard (we have mutual friends), he is successful and married.

I honestly wish the best for him because he is a genuinely wonderful person. I’m sorry I missed out on him, but I’m glad he broke up with me for himself; he deserved better than who I was then. We had a pretty quick breakup and remained friendly. Sometimes I wonder what would have happened, but it’s pointless to think about it now. Plus I probably romanticize the whole thing a little now since it was a long time ago and I have had some really awful boyfriends after him to compare him to.

My boyfriend now reminds me a lot of him (just because it’s a happy and healthy relationship and he’s goofy and loves me too, they’re not really similar), and I’m sober now, so hopefully I won’t have another round of “oh no.”

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25. I Didn’t Know You Cared!

When he called me up the day after I broke up with him to ask me if I was ok.

Yeah. Mistake I've regretted for 13 years now.

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24. Surprise Ending

I dated a guy in high school who I was very into. We were both really awkward teens though, so he wouldn't kiss me and I broke up with him because of it. We'd been really good friends before dating but afterward, he didn't speak to me for about a year.

He was a few years ahead of me in school and he'd graduated by the time we broke up, so while we gradually started texting again the first time I actually saw him was at a friend's party. He'd gotten way hotter somehow. As soon as he saw me he strode across the room and kissed me.

That was seven years ago. We now live together and have three annoying cats.

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23. I Love Him, I Love Him Not

I had some personal issues and thought I wasn't really in love with him. Turned out I was and really regretted my decision to end things. After a few months though, we ran into each other and I asked him for a second chance.

We're together for almost a year now and everything is going great!

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22. Second Time’s a Charm

Mine is tremendously dumb. We were 18. I didn't think I had that same love feeling and we were headed to colleges an hour apart, so I thought breaking up was the right thing to do.

A few weeks later we're chatting and lightly flirting on AOL instant messenger when she misspelled touché as "tushey." I laughed so hard at this mistake that it made me miss her. She also informed me of a guy she'd had a few dates with, so there was some jealousy. I asked her to a movie to talk (dumb, I know) and I felt a strong attraction again.

I kissed her in the parking lot after and we kind of restarted but with a better foundation. We've been together ever since and celebrated ten years of marriage over the sumner.

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21. Lesson: Don’t Be an Idiot

I left her for someone else because I'm an idiot. The other girl turned out to be a jealous, mentally and physically abusive psychopath who eventually ended up in a psychiatric hospital. My ex, quite rightly, refused to take me back.

Lesson learned.

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20. Trying to Look Cool, End Up Being a Fool

We were on a break cause I was being a jerk. In order to get a reaction, I ended the relationship status on Facebook. That resulted in the complete end of our friendship and all. I’ve regretted it ever since. It's only added years of misery to my life.

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19. Perfect is the Enemy of Good

Ten years or so ago, when I was 24-25, I dated girl A for a while. She was cute and sexy but kind of boring in bed. So I started seeing girl B who was fun and freaky, but more unpredictable. I, being stupid, dumped girl A for girl B. I do regret it because she was a good person and I was a jerk for what I did.

I wasn't ready to settle down in any shape or form, so it fizzled out with girl B as well. I think back to some advice my buddy gave me (after all this): if you find a good woman, lock her down!

Now I'm almost 35 and still single. I've accepted my fate as forever alone and just kind of do whatever I want when I'm not working. My best buddy is a 70 year old ex-IBM guy who looks like Benjamin Franklin.

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18. A Little Change Can Go a Long Way

Not me, but my girlfriend. She broke up with me because she said didn't deserve me as she ALMOST cheated on me with another guy. She got rid of the other guy immediately though. She told me she needed time to get her act together. I said I'd wait. That was three years ago, now we are happily back together.

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17. Your Other Half

When I realised that I can’t be the same person I was with my ex with anybody else.

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16. Always Have Your Priorities in Order

One of my exes I just never made time for. She was a great girl and we got along well, I just had different priorities at that point in my life.

She brought it up to me twice and put in effort to fix it. She tried scheduling dates, sat me down and talked to me and explained why she was feeling hurt. And I'd change for a week. But then I'd go back to my old ways. I just wasn't committed. I had other focuses, namely my career. Finally, she just said she still enjoyed my company but couldn't call seeing me once a week for 2-3 hours a relationship.

Even after, she tried to stay friends, but the time between my responses got longer and longer until eventually I looked at it and her last text was from over a month ago. I felt too ashamed to respond, though I probably should have.

I don't blame her. She had needs that I was not paying proper attention to. So I guess it's more like she broke up with me, but she didn't want to and only did so because of my behavior. I forced her hand by just not being around.

The important thing was I learned from it. I learned I needed to pay more attention to my partners. I learned that just because I am very long-term focused does not mean that I can ignore the more immediate concerns and justify it with "I'll pay it off in the long run." And that is a lesson that has led to greater success in this area since then.

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15. What Am I Looking For?

I think I was looking for something perfect. I don't know if I was wrong or not. She was a homebody and I'm a very active social butterfly. She also had some depression problems and we both felt like I wouldn't be able to support her in a way that wouldn't come across as me just waiting for her to get better.

Now I just wonder, mostly, if I really know what I want or if I have a romanticized skewed version of love that I'll never really achieve.

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14. You’ll Always Wonder What If...

It all hit me when my ex died in a car accident. We were married for almost six years. I was so young, had no idea what I was doing. I wanted a divorce and can’t even remember why. Our son was seven. Now he’s 18. He was the kind of man that was good at everything and a very hard worker. A man’s man and a family man. Before he died, we were talking about getting back together. He was my best friend.

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13. Tough Decisions Hurt

I had a realization about my breakup that has been messing with me mentally for a while, but it's also been an enormous eye-opener because of how unhealthy our relationship was. She validated and encouraged me in everything, but never pushed me. I got complacent in a lot of lazy, losery behaviors because she accepted it, so why should I change anything?

It's taken me a couple months to realize: I didn't break up with her because I was sick of her, I broke up with her because I was sick of who I was becoming and how dependent I was on her to feel good about myself. The simple fact of the matter is that I would never pull myself out of this hole of self loathing if I didn't force her out of my life. That being said, I miss that unconditional support and it is almost impossible to go on at times without it.

It still stings every day, but at least it’s usually always a little bit less than the day before.

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12. Loving Partners Don’t Grow on Trees

When I realized that it’s more difficult than I thought to find someone that you truly connect with, like we did. And when I realized that dating and having sex with other people really sucks. It’s not nearly as easy and exciting as it looks on TV. It’s really hard to find someone you like and want to be with. We had our problems, but some things about him I can’t find anywhere else.

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11. Why Does Life Have to Be Like That?

When I started dating other people, I realized I had made a mistake. She was my first love. Two years in, we broke it off as I was heading for college and she was still in high school. By the end of the relationship, I was putting myself way ahead of her in terms of priorities. I treated her like she wasn't as important as she was. Cut to almost ten years later, she's engaged and living across the country. I lost the sweetest, most beautiful, intelligent woman I will ever know. She's the only person I've dated who I ever cared about that much.

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10. Blinded by Beauty

I was a stupid kid. A really hot girl decided she wanted to date me, so I broke up with the other girl to date the hot one. Hot girl turned out to be shallow as heck and we broke up not long after starting. Other girl ended up being basically my dream girl. Absolutely beautiful, smart, funny, great personality, down to earth, etc. She and I remained friends for a long time, but even though she still had feelings for me, she wouldn't actually get back with me because she never trusted me again.

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9. Sex Isn’t All That Matters, Buddy

Someone I know left his wife because he felt the intimacy was awful and he wanted someone with whom he felt he could have great sex. Wife pleaded with him to stay (no kids) but he refused and filed for divorce.

Divorce is finalized about a year later. This guy dates lots of women, but still finds the sex unsatisfactory.

Meanwhile, ex-wife meets this other guy about a year after the divorce and they have that type of whirlwind romance that truly is like something straight out of a rom com. She marries this new guy, they have kids and the perfect marriage. She tells everyone that the divorce was the best thing that ever happened to her and can't believe how happy she is and could never have previously imagined that a marriage could be so wonderful.

The guy, who is my friend, is more miserable now than ever. Constantly says what a mistake he made leaving his wife. Doesn't even go on dates anymore and has not had intimate relations in years.

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8. I Dare You to Screw Up!

I dated a girl I had a lot of chemistry with, and I dumped her on a bet from my friend because I didn't want to come off as "whipped." Honestly, I don't think we would have worked out in the long run, but it still felt like an awful place to end.

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7. Major Return on Investment

When I was 16 I briefly dated a girl who was 17. She wasn't in my peer group; she was an "outsider." But she was nice, had curly blond hair. I liked her. She had an old 1970 Cadillac and she let me drive it. I had never driven before, so maneuvering that giant boat on the narrow streets of town was... fun. After a few months, my friends were bugging me about why I was wasting my time with this girl. She didn't smoke or drink or listen to hard rock. So I let us drift apart. She turned 18, graduated high school and then won the New Jersey state lottery for $6M. I should have stayed with her. My friends were all bums.

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6. Don’t Get Around Much Anymore

It hit me when I noticed that  two years had passed and she's still the last person I'd slept with.

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5. Don’t Sweat the Small Stuff

I broke up with a woman I was head over heels in love with over something that, on reflection, was fairly minor. Spent half a year progressively dropping into a deeper and deeper funk. Wouldn't admit it to myself, but I had clearly made the wrong choice.

I was hanging out with a friend when she pointed out to me that she had never seen me as happy as I'd been when I was with my SO. Another friend pointed out that same week that the music I'd been DJing had become much more depressing over the past few months and asked me if something was wrong. That woke me up and made me realize how special she had been. It took another year for me to realize she was the first woman I'd really loved in the way you come to love somebody for who they are, rather than what you imagine them to be.

I never saw her again. I wish I'd never left her. We only would have had six years together, as she came down with cancer that eventually killed her. It didn't change how I felt; I'd take those six years with her in exchange for all the years I have left if I could.

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4. It’s Not You, It’s Me

I was dating this girl for three and a bit years, and we were doing great.

We left university and she got a job and I didn't get one (for a little while). I got pretty depressed during this time. I went to the doctors and got some help, but it was too much of a strain and I couldn't cope, so I ended the relationship on a very bad day.

I got better and tried to get back in contact with her, but she never contacted me back and ignored me. It makes me extremely sad sometimes as I haven't found anyone else and don't think I will. It's been two years now since and I still get the urge to try something, but I know it's best for her if I don't try.

She has most likely moved on and is in a better place without me.

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3. What Are You Waiting For? Block Him!

I was the dumped one.

Guy and I had a good connection. I actually really liked him. We had a lot in common. But he ended up ghosting me.

A year and some months later, I get a text and it's him. He's asking how I am. I get the vibe he's looking for a hookup. But I'm in a relationship and tell him to leave me alone.

He still stalks my Snapchat stories on a regular basis.

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2. Sudden Change of Heart

In this case, I was the one who was dumped but I love telling this story.

Got dumped by text by this girl who I'd really, really liked for about a year. We were dating for a while when she decided to end it via text with no explanation at all, although I found out the next day she was seeing her ex all the time we were dating. A month after that, I won the lottery. Never seen someone backtrack as quickly. Told her to get lost.


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1. Life Is Totally Unpredictable

I ended it because of school. We planned on getting back together after he was done with school, and I planned on talking to him during summer break. I never saw him or spoke to him again, though, because he died just before the semester ended.

12 years of friendship, eight years of dating. It seemed like a good decision, and I missed him, but we were doing pretty well. And then I got a call from one of our mutual friends. He told me to sit down, and he gave me the news.

It might have been the right decision at the time, but I regret not calling him, texting him, telling him the whole thing was stupid and that I missed him too much during those nine months before he died.

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