Men of reddit, what are your biggest relationships regrets?

28 comments

1. Getting married

2. Both

3. There were 3 or 4 women I wished I would have been more thoughtful towards

4. Not marrying my “college sweetheart”.

5. Dating a spoiled entitled rich girl

6. Not sticking up for myself

7. Letting love blind me of red flags. People will tell you how they actually feel with their actions, not their words. Remember that.

8. Being in serious relationships before my 30’s..

9. Giving a cheater a second chance.

10. I married the first person ever to show interest in me because I thought I’d never have another chance at happiness. I hid my emotional needs, so that the relationship appeared healthy. After marriage, I revealed them. She wouldn’t meet them. The marriage fell apart.

    I was with her for my entire 20s. It’s been three years since the divorce finalised and I haven’t been able to get past the third date with anyone. I’m simply nowhere near attractive enough, for a variety of reasons.

    The damage was done earlier though; the specific things I regret are:

    * Single sex education, especially combined with poor diet and fitness. I spent my entire teenage years hiding from a social totem pole I was permanently at the bottom of, and never got to learn first hand how critically important it is that a man be physically attractive.

    * Not asking for what I actually wanted in my relationship and fighting properly about it. I should have broken up with my ex-wife far earlier.

    * My career is basically a mistake. I’d now say: assume everyone over 50 is an asshole until proven otherwise, and never work for a company run by over-50s unless you intend purely to cynically earn as much money as possible, then leave and start your own.

11. The ones I talked myself out of pursuing.

12. Always taking the safe path in life good education, nice salary, safe career path, bever getting tok much danger, staying in my comfortable zone.. Still young 23, but has gotten to the point if my 10 year old self could look at me now prob consider myself to be a big loser/failure. All choosing thr safe path has left me with anxiety/regrets/just generally feeling numb now.

13. Not following through on my breakup the first time, she fucked me up

14. Not fucking more girls and getting kinky before settling down in a monogamous relationship. In particular, there was one trans woman I was into that ultimately kind of fizzled. I’d have also liked to get into a multi-partner thing to see what that was like. But now the window for those are firmly closed.

15. Forgiving a liar and giving them more chances because I still wanted to be with them. Not turning the other way when my partner was toxic and abusive. Basically as someone else said – letting love blind me of red flags.

16. We lived about 90 minutes apart, and I could have made more of an effort to go see her more often. I could have also made more of an effort in my life in general because I was jobless when we were dating.

17. Not having punched her in the face the first time she cheated on me and tryed to guilt trip me?

18. Not being there for her more. She was always there for me but towards the end I was mentally check out, generally speaking. I checked out with everything and I stopped trying with everything. She was great but it is what it is I guess. Just gotta do better and not follow that same road

19. Getting Oneitis, a women consistently disrespecting me and my needs because I thought “she was the one” lol.

20. Not ending my previous relationship much sooner. I don’t think either of us were particularly happy with our relationship for at least the last year that we were together but it was sometime after she ended it that I finally realized that. We both ended up in relationships that were better fits not long after we split.

21. Letting her know how much I loved her. It was a highschool gf, we were together for 2 years. I would text her I love her but I never shower her off on social media, took her to my family, and just doing the simplest things. I will tell her I loved her but lacking to showing her how much I loved her is my biggest regret.

22. Marriage.

23. Not comprehending my fiance was suffering from chronic depression compounded by Postpartum Depression… I had no clue why she acted the ways she did and it was starting too affect me, and I ended up breaking it off… that was 50 years ago and still wish I could apologize…

24. Recently split with my ex girlfriend. She was psychologically abusive for the last 1.5-2 years of our relationship.

    1. I wish I had stood up for myself more towards her. I took a lot of shit which I shouldn’t have done. I tolerated way more than the vast majority of people would have.

    2. I should’ve ended it sooner. I legitimately didn’t want us to break up – I had the intention of marrying her one day, raise a family etc. Nonetheless she treated me very badly at some point when she clearly had mentally checked out of the relationship but wasn’t responsible about actually ending it when she had checked out.

    3. I should’ve taken better care of myself. Part of my lack of self care was clearly my own fault but with the abusive dynamics I was in I fell into complete disarray of taking care of myself. I also need to be better at communication and nipping my anxiety in the butt. I also shouldn’t had bottled/suppressed my emotions as a coping mechanism.

25. Not meeting my current partner sooner and thinking I needed to just ‘sow my oats’. You don’t need to have anon sex to be happy or feel like your gonna miss out on something

26. Look at the previous relationships. See if she had them for long term or short term.

27. The way I broke up with my ex was really stupid.

28. Still not landing that really rich man to take care of me or at least let me in his will