9 Men Open Up About Their Most Painful Break Up (And How They Got Over It)

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1. “I was with my girlfriend for five years and was seriously thinking about getting a ring. To this day, she’s still the only person I’ve really been in love with. She broke up with me totally out of the blue with no explanation and it felt like someone ran me over with a truck. But I didn’t want to dwell, so I drank myself into a stupor most nights and had sex with whichever attractive woman would look my way. Not saying that got me over it, but it sure helped.” — David


2. “I was so miserable, I barely did anything. Like, anything. I don’t know why people think women are the only ones who grieve after a break up. I was a mess. I barely slept or ate. I guess with enough time, I got better but I’d be lying if I said I didn’t still miss her.” — Howie


3. “I fucked up and cheated. I still don’t know why I did it. It wasn’t worth it. And it ruined a really good relationship with a girl I cared about. I wouldn’t admit this to most people, but I actually started going to therapy after it all went down. It’s still a process but at least I’ve started taking ownership for my mistakes and trying to learn how to avoid making them in the future.” — Christian


4. “I loved her. She liked me, but didn’t love me back. I’m still not over it.” — Ben


5. “We were constantly off and on, but this final ‘off’ was a lot more final. When things were good with us, they were amazing. When they were bad, everything was horrible. My buddies were actually a big help. We didn’t have the long sort of talks girls probably do with their friends, but they were totally there for me. And it’s not like it was all going out and getting wasted. They’d just come over, buy a pizza, watch TV with me. Having people who can keep you distracted after a break up is really, really awesome.” — Ty


6. “I guess the most simple explanation is he fell in love with someone else. When you lose someone like that, not only is it incredibly painful because you’ve built a life together, but it also tests your self-esteem. I felt utterly worthless. I was a miserable, moody thing. But eventually I stopped throwing myself a pity party for one and put myself back out there. I met someone who loved me the way I deserved. I think your worst pain can sometimes lead to the most beautiful moments. I’m so very happy now.” — Sebastian


7. “To this day, I’m not really sure why we broke up. The most I could get her to say was that she wasn’t happy, but even that wasn’t super clear. She was the most amazing woman I’d ever been with – intelligent, career-driven, kind. Losing her fucked me up big time. It felt like if I couldn’t make her happy, was anything else worth it? In the past, I’d gone out partying or tried to just hook up with people right away. But this time I was just single for a while. But actually single. I didn’t date, not even casually. I just lone wolfed it for a bit. I’m not gonna say it wasn’t hard or lonely, but by dealing with my feelings on my own and not finding an emotional crutch, it was a more sustainable way to move on.” — Mo


8. “I found out she’d been cheating on me for three months. We tried to work through it, but I couldn’t regain trust. I was (what I felt was rightfully) jealous about everything. But when we broke up, it was heartbreaking. I did the typical dumb drunk shit and hooked up with a few girls. But that wasn’t really helping. I booked a flight back home (I live in California but my family is from Vermont) and spent a month there. Being with family, the people who love me even at my worst, was very helpful and gave me a new perspective. I can’t thank them enough for getting me through that time.” — Bo


9. “Honestly? I’m still waiting for the day I stop missing her.” — Keith TC mark

Ari Eastman

✨ real(ly not) chill. poet. writer. mental health activist. mama shark. ✨

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