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Dating can be difficult. We jump through a bunch of hoops just to find someone worth spending an evening––let alone years––with and it can feel exhausting. And whether we like it or not, most of us are going to contend with the emotional rollercoaster of accepting that we've been with "the one that got away." (Believe it or not, it was probably for a good reason, even if you didn't see it that way at the time.)

After Redditor TJGaming084 asked the online community, "Have you ever broken up with someone and later regretted it? If so, why?" people shared their stories.


"I wouldn't say I regret it..."

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 abusive 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.

Your_Mask_Is_Tinfoil

"Dated her for 6 years..."

Yeah, she was my first girlfriend. Dated her for 6 years, nothing wrong with 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.

YeahSorry930

This hurts.

Been through it myself––realizing that other people don't compare sucks.

"Broke up with my girlfriend..."

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.

Zazenp

"I think likewise for her."

I ended what had been a couple of years of a toxic relationship. It had been impacting my friendships with others. I think likewise for her. We never actually fought with each other so it was hard to see for a long time. But in the end, we were holding each other back and needed to go our separate ways. Five years later my life is so much better.

Yet I've regretted it since the day it ended. Luckily she moved far away and we both know it's best to not stay in contact online. I think about her a lot though and regret it had to end the way it did.

bg_j38

"I broke up with her..."

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 an unhappy feeling like I was 'never' going to get to experience sex, 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 sex 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) sex matters, and sexual incompatibility can ruin relationships

And b) sometimes, a relationship can be broken badly enough that it can't be fixed.

Sanguine1

I could have been part of..."

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 hateful relationships.

I wasted my youth and can never get it back.

Theearthhasnoedges

No you didn't, dude.

We just make choices––and some of those choices can sting more than others.

"A couple months in..."

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 of 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.

ThorOdionHound

"She accepted me for the most part..."

Yes and no. 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 for 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.

budweener

"I still have the flask..."

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.

JimmyJT35

This is rough.

I still have a couple of mementos from a previous relationship and part of me was, for a long time, torn between deciding whether I should get rid of them. In the end, I figured out how to cope.

"My most recent partner..."

Yes.

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.

With_Trees

Relationships can be difficult.

And sometimes, believe it or not, you might not be in the right headspace to accept even the kindest person into your life. Even those who might seem perfect for you won't find a place in your life if you're not at the point where you feel comfortable with yourself.

Have some of your own stories to share? Feel free to tell us about them in the comments below.

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