Thought Catalog
February 8, 2017

13 Men Reveal Their Biggest Regret About The One Who Got Away

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Allegra Messina
Allegra Messina

1. “Well obviously I didn’t appreciate what I had until after she left, but aside from that, I think just letting her leave is what I regret most, or not trying hard enough to make her stay.” —Patrick, 26

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2. “It’s tough when you imagine your life with someone, and then it doesn’t work out the way you wanted it to. It’s like we create these little dream lives in our heads and set these expectations, and then when we don’t meet them we feel like failures. I don’t regret anything about my relationship with her, I regret expecting and imagining a future that was completely unknown and then being disappointed with the result.” —Alex, 27

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3. “I think people underestimate how hurt guys get in breakups just because they’re guys. We dudes hurt too. We think about the ones who got away just as much as women do. I think about mine almost every day, and I haven’t found a girl like her since.” —Sam, 25

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4. “I don’t like to use the word regret, but I definitely could’ve tried harder in the relationship. When they say relationships are work, they’re not kidding, whoever they is.” —Tony, 26

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5. “I think my biggest regret is that I got too comfortable. I confused comfort with effort. You can be comfortable with each other which is what’s awesome about relationships in the first place, but you can’t forget about putting in effort just because you’re comfortable.” —Dylan, 28

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6. “I have no regrets when it comes to the one who got away. I like to think of her as the one who chose to leave, not the one who ‘got away.’ It was her decision. What am I supposed to do, beg and grovel?” —Luke, 25

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7. “I regret not dating other people ‘too soon’ after we broke up because I was worried it’d get back to her. Had I known that she was Tindering up a storm, I definitely would’ve gotten back in the game a lot sooner.” —Jeremy, 24

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8. “I think people need to stop referring to their significant others or exes as ‘the one’ or ‘the one who got away.’ That literally is the catalyst of regret. That exact label makes you feel like you did something completely wrong because this person was somehow meant for you…and that feeling sucks. ‘The one,’ is a stupid idea in your head, and when they ‘get away,’ you should just think of them as another person you’re not compatible with.” —James, 26

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9. “The one who got away, is never coming back. There’s no use in listing off your regrets about them.” —Nick, 25

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10. “Letting marriage scare me. I guess I thought marriage and a wedding would change things, but even if it did, at least she would still be in my life.” —Theo, 28

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11. “Letting myself fall in love with her at such a young age. If I never fell in love with her, I wouldn’t have to wonder what she’s doing, or where she is in life, or if she’s married with children, or single with a dog, if she’s happy or miserable. Wondering fucking sucks.” —Victor, 25

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12. “I’m a big believer in everything happening for a reason, and if we both couldn’t do enough to stay together, then maybe we weren’t right for each other at all.” —Robbie, 27

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13. “Biggest regret, not telling her how much she meant to me every single day. That I’d literally do anything for her, and that I could see myself being with her forever.” —Daniel, 26 TC mark

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