Random Moments Men Regret Letting A Good Woman Get Away (14 items)

• (#1) He Thought He Was Too Good For Her... Until He Saw The Other Options

  From Xlukethemanx:

  I was a little sh*t who thought I was too good for her, and left. She was my first real girlfriend so I didn’t really understand what I was getting into. Then I have 9 months of HORRIBLE relationships and hookups and realized the mistake I made. I waited until she was single again and got her back, promising that I wouldn’t let her go this time.

  We celebrate our 9 year anniversary this weekend, bought a house, and are getting married next year.
• (#2) He Let Her Go Because Of ONE Flaw

  From V*ginalRiptide:

  I had a single issue with one of my girlfriends. ONE flaw I didnt like. Holy sh*t, nowadays I probably accept 5-10 flaws as not bad. Godd*mn I wish I knew how quickly the good women would get snatched up! Nobody to blame but me...

  I was 22 years old and she was 19. She wasn't jaded yet from bad relationships. Nothing but fun, loyalty, love, trust, appreciation, all of that. Nowadays I am involved mostly with women 25+ and goodness me, most of them just are not quality to be honest with you. Lots of baggage and issues and expectations. All the really beautiful and fantastic women got quickly wifed up, and for good reason.
• (#3) He Had A "Grass Is Always Greener" Moment

  From throwawaysaddayz:

  It started as a tough but amicable breakup that I initiated. I felt I was not ready for a serious long-term relationship and was getting 'grass is greener' feelings and the relationship was at a lull stage. It was my first relationship so I didn't know what these feelings meant or how to navigate them.

  After a month I came crawling back to her (messaging) to ask for forgiveness and to ask if we can try again. After what seemed to be a hopeful few weeks of texting the proposal was ultimately rejected. In so many words she said she was too hurt and the trust is too broken.

  My regret after the breakup stemmed from my feelings telling me all we really needed was time apart and that I took her for granted. That I didn't actually do anything to fix the situation when we were in a lull. That I didn't actually communicate how I was feeling. That love is not necessarily like a Disney movie. That I couldn't answer what someone else has that she doesn't? So yes, these are all mistakes I will live with.

  She has stuck true to no contact except for a few weeks when I broke contact, and I had hope of fixing things.

  Now I am the pathetic ex who broke her heart and came crawling back only to be kicked to the curb. She has kept her dignity. I have not. My attempt to fix things probably diminished her opinion of me.

  So now I guess it's many many lessons learned. And I know its over... but still I get shreds of hope. But I know it is without a doubt over.

  And I know it probably wasn't meant to be, and I know if I did get back together it would probably be a disaster. And I am only feeling this way because I'm lonely. But what if?

  Doesn't matter now it's over. Over over over. She doesn't care about you anymore and you don't matter.

  She will find someone soon and she will look back and be happy it never happened.

  And eventually so will I.
• (#4) After Their Breakup, He Hooked Up With The Someone Else

  From uberphaser:

  Yeah, a relationship I had when I was about 25 or so got rocky, and ended. I was really sad, and thought I had no chance to get back together with her. It was ugly. A few months later I started hooking up with a notorious "village bicycle" (her behind-her-back nickname was "The Wh*re of Babylon") and word got around.

  I got a nasty email shortly after from previous SO that said basically "well NOW I'll NEVER get back together with you."

  I'm not sure what i regret more, the fact that our relationship flamed out so terribly, or that I hooked up with the Wh*re of Babylon shortly thereafter. Either way, it took me about 10 years to fully get over.
• (#5) When He Started To Imagine His Ex With Other Guys, He Panicked

  From StudebakerHoch:

  Long, cohabiting relationship. We were fundamentally unable to resolve conflicts without protracted shouting matches. It wore me out. I gave up trying to preserve the relationship. She moved out. We stayed friends. Months passed, and I started to imagine her dating other guys. I panicked. Tried as hard as I could, within respectful boundaries, to get her back. I was unsuccessful.

  I'll tell ya, I just went to pieces. I can't remember ever feeling so sad, before or since. It was extremely difficult not to let thoughts of her intrude in my life without her. Had to break off contact entirely. This, too, was difficult, as we shared hundreds of mutual friends.

  And yet... I now believe that it was all for the best. Slowly, I recovered. When I imagine an alternate timeline in which we reconciled, it looks very grim indeed. I think we were (and we remain) just too different to be compatible. Although I don't involve myself in her life, nor interest myself in her activities, my friends tell me that she's doing well. And I'm doing well. There are conditions in my life that I'm working on changing (trying to change jobs, trying to buy a house, etc. - nothing really dire, in other words), but I'm certain that I'm much happier now than I was during a majority of our time together.
• (#6) This Guy Didn't Know How Good He Had It Until It Was Too Late

  From SantasDead:

  The women I've dated in the years since. She was amazing, never once did I not trust her. We made an amazing team and our kids got along great. I think I knew she was awesome when we went on a road trip, 5 hours in the car felt like 5 minutes.

  I f*cked that relationship up, not a day goes by that I don't regret it.
• (#7) He Was Too Casual About Abortion

  From Anonyb11:

  I was in a serious relationship with a girl for a while. We shared dreams about marriage, having kids, etc.

  We were 19 and one day over the phone she brought up a "what-if" scenario. "If I got pregnant what would you do with our baby?" I tried to think about it rationally, instead of emotionally. I said if it was early on in the pregnancy I would consider aborting, but if it was further along and I felt I was killing a baby I would def keep it. It depends.

  She was mortified by my answer; the idea that I even considered abortion was monstrous to her. I was just trying to have a conversation and she took it out of proportion, imo.

  She didn't talk to me for a couple of days till she called me out of the blue to break up, blaming me for not loving her.

  In hindsight I wish I answered the question differently, years later now having a child and would never consider abortion now that the situation is actually real.

  After a couple weeks of breaking up she found someone else, she has been with him ever since, years later.
• (#8) He Traded Her Out For A Hotter Girl Who Was A Dud

  From monarch_j:

  I was a stupid kid. Really hot girl decided she wanted to date me, broke up with the other girl so I could date the hot girl. Hot girl was shallow as hell 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.

  Me and her stayed friends for a long time, but even though she still had feelings for me, she wouldn't actually get with me because she never trusted me again.
• (#9) He Screwed Things Up With A Good Woman

  From MrNerd82:

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

  I wasn't ready to settle down in any shape/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 that sh*t down (get serious/married etc)

  Now I'm almost 35 and single... I've accepted my fate as forever alone and just kind of do whatever I want when I'm not working. My best and only drinking buddy that's local is a 70 year old ex-IBM guy that looks like Benjamin Franklin.
• (#10) 10 Years Ago, He Left A 10/10 For A 10/10 Crazy

  From ajame5:

  I became good friends with a girl at 18 and we started meeting up a lot. We'd laugh and chat for hours, but we just kind of bumbled along, not really making anything official of it.

  Then a fun, wild girl comes along and I decide this new one is the one for me.

  Turns out the one I picked was a sociopath - cheating and all the things you expect. She had such a silver tongue though - when I look back now she was so manipulative it's unreal, but I just didn't see it.

  Part way through this relationship, girl 1 could see how toxic this relationship was and offered me a lifeline. She said I should leave and maybe in the near future we'd give it a go when things have died down and my head was right. I stupidly didn't take it, girl 2 had got so far inside my head that I wanted to 'give it a go' and 'make it work'.

  It ended naturally anyway 6 months later when I decided to go to university and get away from it all. By this point though, girl 1 was also in a relationship and would live hundreds of miles away so we went our separate ways and didn't really speak again.

  Fast forward 7 years, girl 1 was crowned Miss 'large city where she lives' and had blossomed into a real 10/10, in looks and as far as I could tell, personality. She was also studying to advance her career, doing volunteer work and all-round goodness. To contrast that, Girl 2 (crazy one) has just had a child named my name in real life. Totally weird but 100% not mine - phew.

  10 years have now passed and we don't speak anymore. In fact, the last time I spoke to her was 6 years ago congratulating her on appearing on TV.

  I probably think about it more than is healthy and it's probably through rose-tinted glasses but what I wouldn't give to relive that and make the opposite choice or even to relive those first few months and see what could be done differently.
• (#11) They Couldn't Figure Out How To Communicate

  From Janube:

  In seven relationships, there was only one in which I told my partner I loved her. We shared a lot of nerdy interests, but the thing I'll always miss most about her is that we shared a sense of humor and playfulness to an extreme extent. I absolutely loved being around her when things were good.

  But, we weren't emotionally super compatible. I need/thrive on communication when it comes to problem solving/mitigation, but she wanted to keep everything to herself. When conflicts emerged involving each other, she was avoidant- she didn't want to approach those conversations at all. It seemed she was able to vent about them on Twitter and then either get over them or repress them well enough to not need to deal with them.

  On the other hand, I couldn't deal with problems without discussing them and doing active damage control and figuring out proactive solutions- to the point where there were a lot of things I couldn't let go of.

  In the end, the communication broke down so thoroughly that I don't think we enjoyed being around each other much for the last couple months.

  It all sucks because I'm still certain I love her, and I miss her every day, and I just want to watch TV and hold her hand while she teases me about something stupid I did or said. I wonder so often if we could have made it work if we had just tried harder to be more accommodating to each other. I still struggle to not reach out to her every couple weeks. It gets better when I'm dating, but the last three years haven't been kind to me on that front.
• (#12) He Never Manned Up And Committed To Her

  From Chris Kmieciak:

  One of my biggest love regrets was a relationship I had after my second serious one. I started to see a girl and we got along great. The romance felt like something out of ‘Gossip Girl.’ We were basically Chuck and Blair. We'd fight about stupid things, fall apart, but the lust to be together was always there. The whole thing fell apart after I wasn't ready to give her the full commitment she wanted.

  Thinking back on it maybe if I had committed more we would have had it all and gotten past our other issues.
• (#13) The Eternal Game Of 'What If'

  From Dusan Micic:

  I regret not being more aggressive or putting myself out there more. I've run into some really great girls that when I look back, I realize they were interested but I was far too shy to acknowledge it at the time.

  Sometimes I guess you just have to lay all your cards on the table and take a hard chance, or else you'll just be stuck thinking what could've been.
• (#14) He Wasn't Ready For Something So Good

  From Calvindehaze:

  I had a pretty crazy 3 year relationship with a woman who didn't have the capacity to actually care for someone else. About two months after we broke up, I met this girl who was one of the most caring people I know. She knew how to make me feel like a million bucks, and never asked for anything in return.

  But, I had to break her heart because I wasn't in any position to be in a relationship, and I kinda led her on. Not for sex, but for emotional gratification. I felt like a piece of sh*t because there was nothing wrong with her, and she did nothing wrong, and she was really cute, but she had to have her heart broken.

  I still talk to her, and when I'm ready to get into another relationship, I'll be lucky if she'll give me another chance.

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