Author: Nathaniel Harris
Date: April 27, 2025
I’m not one to make bets, especially with strangers. But something about that day on Reddit made me feel impulsive, like I had something to prove. It started off simple enough—just a random conversation on a subreddit, where I was scrolling through late at night, and a guy started chatting me up. Somehow, we got to talking about random things, and it led to the most ridiculous bet I could have ever imagined.
It wasn’t anything serious at first. Just a joke about who could impress the other more, but then we both started one-upping each other. He started bragging about, well, the size of certain… assets. Now, I’ve never been the kind of guy to engage in these kinds of discussions, but he sounded so confident and talked so much about it that I thought, “Why not?”
So, I bet him a picture of my girlfriend. It wasn’t a big deal to me—I mean, sure, she was attractive, but I thought it was just some dumb Reddit banter. In hindsight, I should have known better. I sent the picture and waited for his reply.
And then… he sent me a picture. I wasn’t expecting anything too crazy, but when I saw what he sent, my stomach dropped. This guy? He was massive. I mean, massive. I tried to brush it off, thinking maybe it was a trick or something, but the sheer size of what he was showing left me stunned. I was already feeling uncomfortable, but then came the bombshell.
The guy suddenly typed my name, and it hit me. He recognized her. I had no idea how, but he knew exactly who she was. He then sent another picture—this time, it wasn’t just his… well, you know—he also included his face. And that’s when everything turned to ice.
It was our old roommate.
I couldn’t believe it. This guy I had known years ago, someone I’d shared a small apartment with for a few months, was now the one on the other side of that bet. The same guy who used to be incredibly skinny, practically invisible. The same guy I never expected to have any kind of presence, now was laughing at me from behind a camera, showing off in ways I never imagined. His confidence, his size, everything about it just made my world feel like it was crumbling.
I panicked. I immediately deleted my Reddit account, hoping that would erase the nightmare. But it didn’t. Now, every time I close my eyes, I can’t stop thinking about it. The shame, the humiliation, the weird mix of anger and confusion—it’s like it’s all stuck in my mind on loop.
What kills me the most is that I feel like I’ve lost control over something that started as a harmless joke. It was just a bet, right? But now, it feels like a memory that’s constantly lurking in the background, haunting me at random moments throughout the day.
I haven’t told my girlfriend about any of this. I don’t even know how to bring it up, if I ever do. The idea of her finding out and what that might do to our relationship… I can’t even imagine. Every time I think about it, I feel this weight in my chest, like I’m keeping a secret from her.
And the worst part? I can’t stop thinking about that guy—our old roommate—laughing and sending those pictures. What does he think of me now? What does he think of her? I don’t know if it’s the embarrassment or just the realization of what I let happen, but I can’t seem to shake it off.
It feels like I’ve made a mess, and now I’m stuck trying to figure out how to clean it up.
