People Reveal The Moment They Regretted Breaking Up With Their Ex

Breakups suck. Even when they're the best thing for you and everyone involved is good with it, they're still kind of sad. It's so much worse when you realize the breakup was a huge mistake. One Reddit user asked:

What was your 'oh sh!t' moment when you realized you shouldn't have broke up with your ex S.O.?

The responses were rough, honest, heartbreaking, and eye-opening. The sorts of things that make people realize they were wrong were shocking. Some of the breakup reasons were really petty to begin with, and Facebook factors into more than one story. In all of that, though, lots of lessons were learned. Brace yourself, some of these stories are really sad or infuriating. But it's not all bad. I made sure to give you at least one happy ending.

You're welcome.

Merry Christmas, Mom

My mom left my step dad. She was always traveling back and forth 2 states over to take her grandma to chemo and during that time his father passed away and they just couldn't reconcile. They loved each other but life, you know?

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 made because he was the only good man she ever really knew. We all have Christmas at their house (seriously he and my mom divorced and he's still grandpa to my sisters kids and we call his new wife our step mom. They're awesome) but my poor mom has to watch them being happy together every year while she lives alone.


Mourning Me

It really f*cked me up when I broke up with my fiance ten years ago because I realized I could never be the same person I was with him, with anyone else ever again.

That sounds emo, but we had so much backstory, so much history, so many inside jokes, so much shorthand for everything. We'd known each other for 15 years.

I had to mourn the loss of a part of me, a whole side of my personality, that I would never get to be again. Besides just losing him.

Obviously you can build history and jokes with new people, but it's not the same of 15 years of history from age 16 to age 32. Those are formative years.

Regardless, it was the right thing to do to leave him. Realizing what I had lost made it even harder. But it was the right thing to do for many reasons that aren't for here.

- LauraMcCabeMoon

The Wedding Photos

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 then 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.

- sleepytimeghee

Lesson Learned

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 S.O, quite rightly, refused to take me back.

Lesson learned.

- caddy1984

Irrefutable Evidence

An old friend left his wife because he felt the sex was awful and he wanted someone who he felt he could have great sex with. 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 from 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 imagine 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 sex in years.

That's a rough way to find out you are bad at sex, but believe me he now knows it's HIM who has work to do in that department. The evidence is irrefutable.

- Analytica0

Changing The DJ's Set

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 at all that I'd 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 in exchange for all the years I have left.

- helldeskmonkey

The Happy Ending

When I saw her at her birthday party with another guy.

It was kind of a mutual-ish breakup; it was my first relationship so I found it kind of oppressive.

Weeks later, I took her to dinner and told her I thought we had a future together and that I would be more committed to the relationship.

We've been married for 11 years now :)

- mercurialchemister


We were on a break cause I was being a dick. In order to get a reaction I ended the relationship on Facebook. That was the end of the friendship and all. Regretted it ever since. It's only added years of misery to my life

- 753951321654987

Overwhelmed And Suffocated

I pushed her away because I got overwhelmed. I don't know if it's an oh sh!t moment, but 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. And with her, I fell back in love with her for a while and I opened up to her about it. She tried to get me to open up to her more regularly about how I'm feeling, but I just...can't.

I fell out again 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 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.

- shieldedroar

The Captions

I checked out his new girlfriend's social media accounts and saw how they were living exactly the same kind of life we had, and also living out things that my ex and I had planned. The difference is she seems so, so happy about it. Her captions about him shows how she treasures him and thinks highly of him, like she's so lucky to have him. He is indeed a good man. But during our time together he hadn't really figured out stuff yet. I felt like I always had to encourage him, to motivate him. I felt that I was always going to be the captain and cheerleader in the relationship.

When I read his current girlfriend's captions, it wasn't an 'oh sh!t' moment exactly, more of a disconcerting feeling of 'Was I wrong? Should I have been happier with that role? With what we had? Should I have not wished for more? Is there even a 'more'?'

But ultimately, I am happy for him. I don't think I'd ever be loved like that again tho.

- likhaanoushka

Missing What's In front Of You

Because I was a very stupid young man who wasn't thinking at all. I had dated her for a little bit before I broke up with her, cause another girl who I thought was hotter showed a lot of interest in me. And it got really messy after that before we simply stopped existing to one another. That girl I left had been my longest steadfast friend who cared about me way more deeply than I ever deserved. Every relationship since then has exposed very deep flaws in me as a person and allowed me to make very fucking stupid mistakes that I wish had never happened. Every so often I think what if, but I'm not dwelling in the past. She now has an amazing man and I wish them the utmost happiness in this life and the next. I have worked tirelessly to reform myself so I never hurt anyone or make the mistakes I did, and also so that if I meet a girl like that again, I don't mess up again.


"I Don't Blame Her" 

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

She brought it up to me twice, she put in effort to fix it, tried scheduling dates, sat down and talked to me and explained why she was feeling hurt. And I'd change for a week. But 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 a 2-3 hours a relationship. Even after she tried to stay friends but 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, I probably should have.

But I don't blame her. She had needs I was not paying attention to. So I guess it's more she broke up with me, but she didn't want to. 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 that I cannot ignore the more immediate concerns and justify it with "It'll pay off in the long run". And that is a lesson that has lead to success since then.


Butt What?

Not me, but a friend of mine dumped his girlfriend of 5 years because he'd never gotten to have anal sex, and wanted to try it, and his girlfriend wouldn't do it because she was in remission from her fibromyalgia and she was afraid that the pain would cause a relapse. His girlfriend came from a wealthy family, and was supporting him financially at the time but apparently anal was just that important to him.

He dumped her and realized almost a year later when he finally met a girl who was willing to let him do anal that he was completely repulsed by the reality of it. He had been in denial that he'd made a mistake before then, but really broke down after he finally did the act. He was broke, and basically homeless (couch surfing). He missed his original gf, she'd been the only woman who'd had the patience to handle his eccentric personality for more than a couple months. He tried to get back with her but she'd moved on. He's never fully recovered in my opinion, he's still essentially homeless and has developed an alcohol problem in recent years.


Should Have Listened

One of the last things she ever told me was "you're going to be single for a long time." It's been 2.5 years. She was right. Not that I necessarily want to be with her again, but she was right that it would be hard to find someone again who'll give me a chance.



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.


With Friends Like These...

The break up was kinda mutual (didn't want to break up with him but, I had no choice.) A few weeks after we broke up, I started to catch up with some friends - all of which tried to take advantage me. The first guy wanted nude pictures of me, the other tried to get me into bed. I felt very sh!tty and disgusted, and couldn't help but remember how gentle and careful my ex was with me.

- mediocrityismyforte

A Mile Down The Road

I hope she sees this.

When I got about a mile down the road after packing all of my things, I truly regretted leaving. We tried to hang on for a month afterwards but it didn't take. She couldn't handle that I just left instead of staying and trying to work on things. It's my biggest regret.

I was too wrapped up in myself to really see what was causing all of our issues, I only wish I could've seen it sooner. I tried to talk to her about it, to show her that I know now what I could do to help mend everything but I caused too much damage and pain.

I hope to see her again one day, but all I can do now is work on becoming the best person I can be. I'm currently working on all of my issues that caused all of these problems. It just saddens me because I know that down the road I'll meet someone new who will have this version of me that I will have put a lot of time and effort into. But in my mind's eye my ex is the one who deserves all of that work from me.

- WhiskeyWallace

Mean What You Say

I wasn't the one the broke up with my ex, but breaking up was always a topic that was there due to long distance. We were talking about the future one day and she was pretty adamant about pursuing her career, which meant she wasn't planning on moving back with me. It turned sour really quick and I threw out a "maybe we should start thinking about breaking up."

The next time I visited her, she told me that she decided - and we broke up. I guess the "oh sh!t moment" didn't hit me until a month after when I tried to win her back by flying out to her (I had to give her stuff back, at least that was my excuse). But it didn't work and might have been even more painful cause it seemed like she had someone else already.

When I got home I sat on a bench in a park and couldn't stop crying. I felt like what I just lost was equivalent to losing my best friends that always followed along with all the dumb childish ideas I had, losing my mom with her undying love and loyalty, losing all the vibrant colors that are in the world that made everything seems so beautiful, losing my dreams of possibly one day having kids (I never really liked kids but I always thought if we had kids they would've been awesome), and then some.

The "oh sh!t moment" lasted for about a year, and I still remember her fondly with no resentment because I was dumb. But I take the advice "say what you mean, and mean what you say" pretty seriously now.

- kevwjj

Mental Health Crisis

I left my girlfriend at the bottom of a debilitating mental health crisis. I guess I just ran out of energy for it and figured if I was good enough to get her, I was good enough to find someone easier and healthier to be with.

Nope. Coming up on five years. She recovered completely, no other woman has shown a shred of interest since then. All I had to do was stick it out.

- iron-while-wearing

H/T: Reddit

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What is the strongest opinion you once held but no longer hold, and what make you change your mind?

Jade-Colored Glasses

I used to think that being cynical/negative was realistic and somehow smarter than being positive. I've since realized that a "be prepared for the worst but expect the best" is far better. We can't control the outcome of anything in life. Being negative makes you miserable rather than protected from bad things happening.


Cant' Have A Conversation With A Parrot

I used to be a conspiracy theorist. Believed that 9/11 was committed by the US government and that we never landed on the moon.

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A Big, Mysterious Universe

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Portrait Of An Artist As A Young Man

I used to believe anyone can be a successful artist if they just put the time and effort into it. There is no such thing as talent, only hard work.

What changed my mind: Art school. There were quite a few people that tried hard, but just weren't able to achieve professional level art.


You're Not Your Emotions

For the longest time, I thought my emotions were in a sense the most "real" part of me. I was always a very emotional person and I didn't make a real effort to control it as I thought it was a good thing, that I was just being honest with myself. Over time though, I started to become very depressed and the negative emotions just keep adding on and on. I thought "this is just how I am I guess". Unfortunately it started hurting other relationships I had, and everything changed when my girlfriend broke up with me. After a lot of reading I found that emotions are not who we are at all. They're just reactions and there's nothing that requires us to act on them or feed them. I'm learning to let it go through me instead of hanging on like I used to.


Don't Forget Big Willie Style

I used to think that hip hop was bland, repetitive, and all about clubbing and sh*t. Then one of my friends pointed me towards people like Kendrick Lamar, Eminem, Nas and Run The Jewels, who all have great songs and clever lyrics, and I realized that Hip Hop is pretty great.


The A**holes Will Always Find A Way

I used to think that the catholic church was responsible for all of the hateful people in it. I gave people the chance to challenge my opinion and someone explained it very nicely to me. Basically, the hateful people use the church as an excuse, if you remove the church they will gladly find another excuse.


High Times


I used to tell myself that I would never stop smoking weed, and that I'd be happy if my kids grew up to be pot smokers... Now I have a kid, don't smoke, and realize what an idiot I was when all I did was smoke all day. I could probably be in a much better position if I hadn't smoked all through college.

But I mean, I still think pot's okay... Just in moderation.


The Road Less Traveled

"All taxation is theft, man! I made my money without any help from public institutions or the infrastructure they support, I should be able to keep every last dime of it!"

Naturally that was when I was 18, living at home rent free, and working at Pizza Hut as a delivery driver who relied upon public roads for pretty much every cent I made.


All Those PSA's Didn't Do Much

The whole D.A.R.E anti-drugs. Yes crack and heroin is bad, but they over dramatized what happens when you do smaller drugs. Weed isn't even a gateway drug, alcohol is more of a gateway drug. When I saw weed for the first time I thought it was tobacco (This was after all the D.A.R.E training too). Letting the government teach you your morales and philosophy is a thing that sheep do. Don't be a sheep.


Where Would We Be Without The Kindness Of Strangers

I used to think people on welfare and state assistance just weren't trying hard enough. I grew up spoiled and entitled and it seemed like any kind of charity was a stigma.

Then, my husband became chronically ill, and the economy took a shit. My family has been close to homelessness more than once, and have relied on state insurance and assistance off and on throughout the past few years. There are definitely people out there who abuse the system, but some just get stuck in a horrible cycle of poverty.

I also work in a school that has a high number low income and refugee families. It has really opened my eyes to the struggles that some people face.


He's Still There For You, The Best He Can Be

I could go through life and could seek meaningful advice from my Dad who has always been there for me.

Now he has been reduced to a feeble condition, I am starting to understand I'm out there on my own, and even what he's sure of is suspect given his mental and physical facilities have been rapidly deteriorating in his late seventies. I feel horrible that I have noticed this long before he did - or at least admitted as much.


Clear Your Mind

This was before I received an ADHD diagnosis. When my doctor referred me to an ADHD specialist, first of all I refused to believe him and was kind of slighted that he even suggested that I could possibly have ADHD.

I had a very strong opinion that if I get a diagnosis that I would refuse to take prescribed amphetamines because they are "bad" and "addictive" and that they would ruin my life.

Then I actually tried the prescription and it was like magic.


Going Through The Whole Spectrum

Used to be fairly open with my views on immigration policy. Then I worked for a while down near Corpus Christie doing immigration work. I'd say one out if every hundred people that came through our office was going to somebody who actually wanted to work and try to make a living here. So many people simply wanted to exist enough to get welfare. Many were young men who we would later defend against exportation as a result of their criminal activity. I began to despise the work of defending these men and wished they would be deported.

Now, I'm dating a foreign girl and we are in the legal immigration process. She has advanced degrees and skills, so that makes things a little easier. But it does make me resent people who just bypass the system. We can't bypass the system because I imagine my participation in immigration fraud could get me disbarred.


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