12 People Share The Moments They Regretted Their Break-Ups



No matter how you slice it, break ups are an awful emotional experience to weather. Whether you were dating three weeks or 30 years, there’s still an adjustment period where you feel the weighty absence of your former partner at every turn. Even the best, most amicable break ups come with a fair amount of pain, and let’s be honest, most break ups don’t fall under that umbrella.

Barring violent or physically dangerous situations, I would venture to say one of the most difficult break ups to get through is one you find yourself regretting. It’s not uncommon to initiate the break up, rip off the emotional band-aid only to realize down the road what you’re missing out on.

In a recent Reddit thread, commenters shared their painful “oh shit” moments where they regretted cutting a relationship off, and it’ll make you feel infinitely less alone about any relationship regrets. While hindsight may be 20/20, I do think it’s important to remember how easy it is to idealize someone when you’re no longer together.

Basically, love is impossible to “win” at and you’ll feel hurt or frustrated at times no matter what, so might as well at least find solidarity with the millions of other people handling the battlefield of relationships.

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.


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 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.


I ruined my relationship with my college boyfriend because of my alcoholism. It had just really started 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 shit” 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 was 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 had some really shitty 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 maybe I won’t have another round of “oh shit.”


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


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.


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.


Not me but someone whom I casually knew from college.

Left his wife because he felt the sex was awful and he wanted someone whom they 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.


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.


A few months had gone by, and I was still feeling like shit about it, cuz I knew she really loved me. However as much as I cared about her, I couldn’t shake the feeling that I couldn’t be the man she needed me to be for her, and felt I was leading her on. I had been OK with my decision. Then I went on a trip to NYC with a couple of friends. It was…not an enjoyable trip, and top things off I found out my granddad had died the week prior so I had to fly back home almost immediately after returning from New York. Suffice it to say, I was ready for it all to be over by day 2 of this essentially 2 week trip.

Anyway, about 3-4 days in my friends and I were out to dinner and they started talking about my ex (they had gotten to know her while we were together, and they still hung out). All I remember was wanting nothing more than to be home already and to be with my ex. That’s when it dawned on me and my heart sank.

Saw her again when I finally got home again after about…4 months, and spilled my guts. Buuuut she had already started seeing someone new in that time. Wound up meeting him at a housewarming party a few months after she and I reconnected, and it turns out she has a type. Her guy and I hit it off immediately XD

Dude and I got super drunk together and I wound up telling him something along the lines of “I really wanted to hate you, but goddammit you’re fucking awesome.” He was a wonderful sport and got a good laugh out of it. I promptly informed my ex of my plans to steal him from her.

Needless to say, this was something like 2 years ago. They got married last month, and I’m happy to report that we are good friends. Do I regret ending things? Sure, but the time and perspective helped tremendously, and frankly she did a lot better in finding him. I love them both dearly, and get a lot of joy seeing the two of them so happy with one another.


When I realized that it’s difficult to find someone that you truly connect with, like we did. And when I realized that dating and having sex with other people fucking sucks. It’s not near 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.


My oh shit moment was when he died in a car accident. We were married for almost 6 years, I was so young, had no idea what I was doing. I wanted a divorce and I can’t even remember why. Our son was 7. I have our now 18 year old. He was the kind of man that was good at everything and a very hard worker. A mans man and a family man. Before he died, we were talking about getting back together. He was my best friend.


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


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