What's your biggest dating/relationship regret?

Such as cheating, not giving the other person a second chance, being too guarded, sleeping together too soon...


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Most Helpful Guy

  • Not realizing how I felt about a girl who liked me. When I finally asked her out, it turned out that she had just got together with a guy. We had a long, warm hug (I barely managed to stop myself from crying), and we never saw each other again. I'm over it now, but I still think about her sometimes.

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    • That's brutal. Thanks for your answer.

    • It was brutal. She wasn't though. She was really nice about it, which made it worse. I wanted to hate her, but of course I couldn't. It didn't help that it was my first time asking a girl out and my first rejection. I've never felt that bad since, though, which is good.

What Guys Said 6

  • I don't have any. I wouldn't want any of it different. Those mistakes, heart breaks, bad decisions, etc. all led me and crafted me to be the person I am today. The man I am today was crafted through pain and I gained more wisdom and self assurance of who I am so that I can be the man I need to be for my wife someday. The arc of life is funny sometimes..

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  • I probably played it way too coolly with my last girl, and gave her too much time instead of taking her in right away, so I never got into a full relationship with her.

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  • Taking girls seriously.

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  • It would be breaking up with my girl because I found someone better.

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  • Getting into a relationship. Dating is fun and you're going out on dates and hooking up with each other, then when you get a title everything changes. All set with relationships.

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  • Not dumping my first serious girlfriend fast because she didn't want sex.

    No, I'm not kidding. Huge mistake that messed me up for a decade.

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What Girls Said 7

  • Getting stuck in the pattern of trying to help a guy (family, finical, work though issues). Even if you succeed in effecting them you often feel resentful, tired, neglected and want out.

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  • Being too jealous and getting mad over little things. It only made him hide things from me and lie to me.

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  • Alll of the above and then some. Oh if walls could talk, what a story they'd tell...

    On second thought, if walls could talk, I'd have to burn them down :p

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  • Mine was dating a man who told me I was perfect. No one can live up to that, and when he figured out that I was human like everyone else he turned mean. Guys who think you are perfect are more prone to turn mean. Lesson learned.

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  • Being too shallow.

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  • Probably dating him in the first place

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  • Being too guarded. I have trust issues, so I always second guessed everything he said and I never fully let him in.

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