You probably have a person in your life who you still refer to as “the one that got away”, right?
And today we’re gonna get a big helping of break up regret stories.
Check out this Reddit post.
Have you ever broken up with someone and regretted it later, if so why? from AskReddit
What are the real stories of the ones that got away? Let’s find out.
1. Right decisions, wrong reasons
I was in a 4 year relationship with someone I always considered to be not-the-one. Turns out it was all fear of commitment. I left the relationship because from the get go, I thought it would be over soon.
It was a great relationship. She accepted me in the most part, we had some personality shocks but I came to accept that I loved her and that I would marry her eventually. Problem is, that feeling of “you’re losing lots of opportunities” never went away and the personality shocks pilled on it. Eventually my fear of commitment got to me and I broke up with her in 2019.
Since then, I learned about that fear, regretted the break up, talked deeply with her about that, and learned that I was not wrong in breaking up with her. The relationship was making me miserable, and having a toll on her too, and it wouldn’t get better unless I learned what I learned this last year, and that would probably not be enough. It was the right decision, but for the wrong reasons.
I don’t regret it anymore. My 2020 would be way less lonely if I hadn’t broken up with her, but I learned a lot about myself and still have a friend in her. We’re not as close as we once were, but sometimes that happens.
My point is, you might miss the relationship later, even if it makes you feel bad now. That’s okay. Just remember that breaking up is as much a commitment as staying together.
My most recent partner was pretty amazing. And he was the only person I’ve ever met who was actually willing to fight for me, and not turn away at the first sign of minor inconvenience.
And I rejected and dismissed him repeatedly, because I was too hung up on stupid things that didn’t really matter.
I could have had the family I desperately need, had I not been a complete and utter idiot jerk.
3. The right thing to do
I regretted it even as I was doing it, but I knew it was the right thing to do.
He was my first serious bf, but we were very young. There was a lot of love, but we’d developed some unhealthy communication and were hurting each other. Neither of us really knew how to fix it or whether it even could be fixed.
I h**ed hurting him and walking away was painful, but it was necessary. The way things were, that relationship was not going anywhere good.
All in all, I regret the pain I caused, but I’m still certain that it was the right thing to do.
4. Evade and avoid
I broke up with my boyfriend because he was avoiding taking care of some PTSD issues he had from his time in the army. When we first started dating, he was talking to a therapist weekly and then slowly dropped off until he hadn’t seen someone for almost a year. I was also not doing well. I felt like I was drowning and I couldn’t see myself carrying him, too.
He got his sh*t together. I made some mistakes of my own. When we started talking again I was picking up the pieces and he wanted to help me. I’d never felt so loved in my entire life. I didn’t deserve him, but he wanted to be there and I finally wanted to let him.
We started over, dating again, working as a team to manage our collective issues. We eventually got engaged and then got married a year later! When I first met him I thought he was the love of my life, and even though the path wasn’t neat and tidy, I wasn’t wrong. He’s the good things- I’m d*mn lucky and I know it.
5. The dog
Yes but not because of the woman I was leaving.
We were together for 3 years and we ran our course, that was fine and it wasn’t that hard to break up. But she had a dog, a tiny little Jack Russel Terrier who was already 12 years old when we I first met her. That dog was my spirit animal and we just bonded instantly. She followed me around everywhere and I love that dog bits.
She was a tough nut but she was really frozen due to age so I bought her clothes so she could be both warm and a bad*ss at the same time. It doesn’t show in that picture but she was really confident in these clothes. When we broke up it sucked because I had to leave this sweetheart behind, she wasn’t mine. And then 4 months later she passed away. The last thing I did was slam the door behind me and I have so much regret in my heart that I didn’t take a moment to say goodbye to this dog, or stayed for another 4 months before breaking up so I could have been there for her at the end. It sucks!
6. The freak out
I regret my most recent break up.
Essentially I freaked out because he ‘liked me too much’ and after a long series of boyfriends and an ex husband that had made me feel like a burden that should be grateful for their presence, I didn’t know how to just enjoy it. Ultimately I sabotaged the relationship rather than let myself ‘fall’ in his eyes.
Which I guess I’ve done anyway.
Yes, I broke up with my ex about 2 years ago because I was going through depression. I needed time to recollect and reflect and I just lost the feeling of being happy and I lost feelings for any relationship I had, whether family intimate or friendly.
I regret it now because she was the best girl I’ve ever dated, but now there’s no chance of going back with her. She could’ve gotten me through those times, but I just didn’t know that. I f*cked up. Big time.
8. Too good for me
I broke up with the love of my life because I thought she was too good for me.
She didn’t think that and tried very hard to convince me I was just scared (she was absolutely correct) but I wouldn’t listen and I pushed her away. It is hands down the worst mistake I ever made in my life. Kids, learn from my disastrous mistakes….and get off my lawn!
9. Underneath the drink
My most recent ex was a really good person underneath what I consider to be an alcoholic, mean girl who didn’t like me all the time. I got into my current relationship right as that one ended, because I realized this new one (current fiancée) actually liked(at first, now genuinely loves) me.
But I regret the breakup, in a way. She had a 2 year old kid and I loved him a lot during the year we dated. The boy’s father was a d**dbeat and cheated on my ex while she was pregnant and then left her for the cheatee. I regret leaving so hastily because, from her perspective, I too left her for someone else. I guess, not just her perspective, as that’s basically what happened.
But I just wasn’t happy and my time with her was a drunken mess of constant fighting and anger. I just know she was a good person down deep inside, just deeply flawed due to a lifetime of being failed by those she loved. And I just added to that and failed her one last time.
10. Something better
Because it was a stupid reason.
She was the most beautiful woman inside and out that I ever met but my immature *ss thought there “might” be something better. There never was…
Had a crush on this girl for 2 years who was affectionate but never displayed any serious attachment. Then I started seeing someone else after I got tired and she was amazing, kind, smart, but about two weeks in, the long lasting crush feelings were still there so I ended the relationship because it felt somewhat unfair towards the girl I was seeing.
I ended up eventually with this crush, I very quickly realized she was the most a**sive toxic person I’ve ever met in my life. I have never with anyone been yelled at so much, fought so much, blamed for the smallest things (she once stopped talking to me for 2 days because I accidentally got off the bus one stop too early when taking her to see a movie, we had to walk 10 extra minutes).
It was over 5 years, I still regret breaking up with this girl who was one of the nicest people I’ve ever met for this a**sive crush…
12. That’s a first
My first girlfriend.
I wouldn’t say i regret it because i am who i am today because of the decisions i made. It took me a lifetime of bad and sometimes a**sive relationships to realize that actually everything i could have wanted and needed was in her.
She was truly a good soul and in my naivety i thought there would be many others like her, but life doesn’t work that way.
Last i heard she had a husband and a kid, couldn’t be happier for her.
13. Beat me to it
Broke up with a girl because she was about to head back to a fancy college and I assumed she’d quickly break up with me after a few weeks there. I was determined to not be the one getting dumped, so I did it first.
Turns out she was devastated and was planning on making a long distance thing work. I felt terrible, but I couldn’t just take it back, so I decided to give her some space.
Half a year later, at Xmas break, we started talking again and quickly got back together. I went back to school myself and we’ve been married 13 years.
14. WTF was I doing?
Broke up with my girlfriend because she didn’t really fit into my idea of who I wanted to be with.
About two weeks later it suddenly hit me, she was a kind person who genuinely liked and accepted me. WTF was I doing!? Asked her to reconsider and she said no.
We remained friends and a few weeks later I asked her to reconsider again. She said no because she didn’t know if I was just lonely or wanted to be with her. Told me to wait a few months and then decide if I wanted to ask her again.
We’ve been married for close to ten years and I’ve never been happier.
15. Give me a chance
I don’t regret breaking up with anyone, but I do regret not giving some people a chance. In my life I’ve had some genuinely awesome women that were interested in me and I let them slip away for toxic and horrible relationships.
I could have been part of a team where we elevated one another and together became better than we could have alone. Instead I just couldn’t stop myself from settling down into toxic and h**eful relationships.
I wasted my youth and can never get it back.
16. No comparison
Yeah she was my first girlfriend. Dated her for 6 years, nothing wrong in the relationship but I assumed something was wrong because she was my first.
I didn’t know what other relationships were like for comparison. So when I started dating other girls I realized I screwed up.
17. Twists and turns
I did. I regretted. She took me back. We married.
Now we’re divorced.
Take away from that what you want, people.
18. Making commitments
Yep, I broke up with my first girlfriend and regretted it.
We were both still virgins, but I didn’t want to be, while she was a devout Catholic who wanted to save herself for marriage. I respected that, but 17 year old me felt unhappy feeling like I was ‘never’ going to get to experience s**, though I still happily dated her because she was my first and I was happy enough to be able to tell my friends that I had a girlfriend.
I broke up with her, but after going through that experience and feeling how terrible it was for both of us, first heartbreak and all that, I turned around and won her back. I did it for the wrong reasons – I felt guilty for hurting her, and felt in retrospect like breaking up over s** was a shallow thing to do.
Thing is, the spark was gone after that so she broke up with me soon after anyway. It was for the best – we were incompatible in other ways that became apparent later – but hearing her say ‘I don’t love you anymore’ was perhaps the most savage emotional gut punch of my young life.
And that was how I learned that
a) s** matters, and s**ual incompatibility can ruin relationships
And b) sometimes, a relationship can be broken badly enough that it can’t be fixed.
19. The hook up
Shortly after the most crushing breakup I had, I found a girl a few years younger than me with two kids just looking for an “adult friend”. I was clear about not looking for a relationship and we started hooking up.
A couple months in I really liked this girl and asked her to make it official. She agreed and I was super into her, but awkward with the kids. She never pushed me to be more involved with them too fast and the kids and I met slowly and then more and more.
We actually broke up a few times. I would end it because it got too scary with the kids and then we would get together and then she would end it because it was feeling too serious. On and off for about two years until I got offered a massive promotion 12 hours away and took it.
We split up “for real”, which lasted about 8 months. Then by fluke I ran into her while visiting my parents and we rekindled. I didn’t even realize how much I had missed her until then. We’ve been doing long distance for about 9 months now and I’m looking for a job back in town. I’ve proposed, she accepted, and she’s constantly sending me links to dream homes we should look at. The kids and I love each other and when she works I’ve been taking the kids to school and picking them up and they both call me dad.
I think the biggest thing that kept breaking us up is that we both went into it refusing to want a real relationship and directly looking to not fall in love, and let our stubbornness and egos (which we both have plenty of) refuse to let us reevaluate or be the first to tell the other we were wrong.
20. Huge mistake
I dated a single mom in 2012-13.
Gorgeous, smart, funny, affectionate, liked everything I did including football and metal. Got me an engraved flask for my birthday with an inside joke written on it.
Broke things off because an ex had come back into my life. HUGE mistake.
Not only did things not work out with the ex but I burned the bridge with the other woman. She blocked me on FB and IG.
I still have the flask and it pains me to look at it
21. The breaking point
Yes and no.
Yes, I regretted it because I missed (and still miss) and loved (and still love) him more than anything.
No, because it was a long time of neglect, and I couldn’t take it anymore.
22. The routine of it
Yes. We were together four years, she was the first person I wasn’t related to that said that they loved me… I was hooked. I was unhappy for a majority of the relationship, I was cheated on, she made me h**e myself.
I missed the routine of it. I missed going to our places. I missed the inside jokes. I missed the friend she was. The friend that attaches to the end of the word “girlfriend”. I am thankful that when she came crawling back 2 years later, married and lonely for me, I was strong enough to say “no.”
23. Settle down
My college girlfriend.
She was my soulmate. She understood me, always had my back, and put up with my BS.
But being young and stupid I thought I needed to sew some wild oats before I settled down
So off I went to sew, and when I was finished, she had already settled down, with another guy.
24. Blind obsession
Not really broken up because we weren’t dating, but at the time, she was a close friend of mine. Used to play video games with each other until late 2015, then we started to distance each other for a bit but still kept in contact.
I completely stopped talking to her around early 2017 because I was blindly obsessed with another girl who became toxic to me a year later and it took me 6 months to recover from that.
Last year, with the lockdown and all, I started reminiscing about my old friends that I have left behind and remembered her. Took me a few weeks to consider if I should message her again because of how long since we last talked, even though we never ended on a sour note.
Eventually messaged her and asked if she remembers me, she said not really (although she still had my number saved), but was still really friendly and pretty much the same person as I remembered from 2015. We still are in contact now but we are both busy with our own studies, and I think she may have slowly remembered who I was before. Planning to talk to her more and maybe meet up with her for the first time by the end of the year.
25. The a**ser
I knowingly dated them while they were in an a**sive) relationship and before i knew about the a**se, I told them it wasn’t fair for me to have them while someone else loves them, and that the a**ser was the better choice.
they came back over a month later covered in bruises and told me about everything, from their partner beating them to cheating and making this person watch, and that they did not feel guilty for coming back to me because I helped them realise that they dont deserve the sh*t their ex put them through. so i got them in the end, but I still feel so awful for sending them back to that h*llhole even if i didnt know. we’re in the process now of getting the a**ser to agree to either move out or let them move in with me.
She was a great girl. I was really sick. Got her to break up with me (hello self-sabotage).
I don’t really regret it because she’s doing well, and so am I… but still, sometimes, I do think of her… and the nostalgia hits you.
I learnt so many good habits from her, we had fantastic conversation (she was oozing brains), she taught me a lot, she was really affectionate and understanding. She tried to be there for me, but I never really let her in. She had her own issues, but overall, she was a fantastic human being, and someone you could grow old with.
I do regret that I am never going to see her, and I am not going to get an opportunity to apologize for the way I was.
Reddit, if you have something to say to someone, say it. Trust me, just do it!
27. Laugh, credit, smiled
Tough question to answer honestly.
Immaturity, mostly. Combined with my own doubts and insecurities. Then life sometimes just gets in the way of your plans when you’re young.
You sometimes don’t understand what you want or need in life. It’s for some, not until you’ve lived a little, (laughed, cried, smiled) a little, until you kind of understand who you are and what you want. Everybody has the story of the one girl who got away. Question is, did you miss out on an idealistic version of a person you knew, or did you find a person who helps you to be an ideal version of the person you would like to be?
28. Granting closure
Regretted not getting back together when she offered. We broke up on a camping trip July 5th some years ago because she was having a hard time with the long distance.
She said she’d still like to be my +1 to my mothers wedding in mid August, and I still wanted her there, so that was the next time I saw her.
On that trip she said she had had the space she wanted to think and she wanted to get back together.
I was still too hurt from the breakup to accept at the time (telling myself that if it didn’t work once it would never work).
I guess that gave her the closure to move on, and we grew apart after that. By the time I got over myself and my hurt feelings, it was already too late.
She’s still the only person I’ve ever been in love with.
29. In retrospect
I don’t regret breaking up with him at the time, but a few years later I wonder “Man, if I was this mature back then, that relationship could have been way healthier.”
30. A sad tune
She never gave me back my CDs.
I should have gotten them back first.
Heartbreak all around. Especially for those missing CDs.
Have you had an experience like this?
Share it with us in the comments.