I am Genuinely curious, what’s that one thing you did in your early days that still makes you stare at the ceiling and think, I shouldn’t have done that.

It could be any embarrassing moment or experience you still flinch when you remember it.
Share if you’re brave enough… I wanna know cause I have some sort of experience and i didn’t know if is it just me or you guyz also experience the same.


27 comments

  1. It’s something I didn’t do actually.

    I didn’t sit with her the first time she said hi to me.

  3. I don’t have many true regrets despite making lots of mistakes as my path has lead to to exactly where I wanted to be at 31, but treating my body like trash, being fat & drowning myself with alcohol through all my 20’s is a regret.

    I’m trying to fix it all now and I do believe that I will, but it just sucks looking back to where I could be if I even cared a little bit.

  7. I was too dumb to understand “soft rejections” from girls. I ended up doing shit like asking them out multiple times. It only got worse after picking up drinking in my late teens. I shudder at the thought of some of those texts. While I get it now young me thought unless it was a direct “no” I still had a chance.

    It wasn’t until I actually got lucky a few times I realized that if she’s into you things work out so much better.

  8. Cheating on my first gf. Luckily I did it when I was young and luckily that’s the worst thing I did.

  9. Stop studying and get a shitty job because having money and going out 4 nights a week is much more fun.

  10. I drove drunk on a boys’ road trip. Not slightly buzzed, but absolutely hammered. From the next morning to today, the feeling of stupidity hasn’t really lessened (nor should it). If I had gotten arrested or, far worse, hurt or killed somebody, I think my life would be entirely different. I dodged a bullet that I fired at myself.

  11. I didn’t buy a house in 2012 ish… after the crash of 08 banks were practically giving them away

  12. It’s mostly education and career-based. I was a smart and dedicated student with a lot of full-ride scholarship offers, but realistically I didn’t put any thought into my future or what I wanted to do, and thought it would sort itself out. I picked a nearby state school instead of any of my awesome other options, didn’t even visit them, and basically found myself with a mediocre degree.

    I didn’t give enough forethought to what something like advertising might really require, and happened to fall into a very math-based profession instead of something that’s more creative, and I’ve constantly been unable to get out of it. I’m currently unemployed because of an injury, but otherwise spend all day in Excel and data, and it drains the life from my body.

  13. This is a story that most people couldn’t waterboard out of me but I’m just going to tell it.

    I was 20, going to college in downtown Chicago around the early 00’s.

    Long story short, one night I took a bunch of uppers, drank a fucking bottle of whiskey and stomped down State street by myself *for hours,* screaming the entire list of the most derogatory slurs imaginable, most in English and even some in Spanish, *at the top of my lungs*.

    I was completely out of my mind. Absolutely no consciousness whatsoever, but I have little ribbons of memory from the night. I’ve never said these words before or since.

    I was walking up to groups of people, snatching their cigarettes and slowly burning them out on my skin, leaving several scars for years on my forearm. I was picking fights with people who would run away.

    I remember at one point, bottles were raining down on me from people in skyscrapers that could hear me all the way up there. Like, glass shattering in the street and Gatorade bottles clanking loudly, with people hanging out of their windows and flipping me off from above. I remember challenging them to come down as well.

    For all intents and purposes, I should have gotten my ass kicked or worse. In hindsight, I was probably acting *so* insane that even the actual creeps and weirdos were giving me a wide berth.

    This memory fucking haunts me to this day. I have no idea who that was. I will absolutely wake up decades later and wonder if anyone remembers. I cannot believe I still walked those same streets for a year before leaving.

    The shame I carry from this event still weighs a considerable amount, and prevents me from ever behaving in such an animalistic way ever again.

  15. I got really drunk one night at a party and said some nasty things to a woman I adored. We weren’t dating yet, but that’s where it was going. I didn’t think I was good enough for her so I wanted her to get over me.

    I was right and she did. I don’t drink anymore.

  16. I stupidly bought a business off my boss when I was 25 and she tried scamming me hard. She got debt collectors harassing me.

    Lucky for me I started dating a business lawyer and she went over things. Realised it was bull shit and turned it back around on the debt collectors, which was incredibly satisfying.

    That said still bought the business and it was a lemon. Learnt a lot so when I started my current one I had a much better launch point

  17. Staying with someone because I didn’t want to hurt them.. staying at a job because I thought I owed them loyalty.. staying friends with toxic people, because I was too scared to be alone.
    Making terrible choices because I thought it was cool (lying, stealing, + drugs)

  19. Sniffing a line of dirty 2cb which burnt the inside of my nostral so bad it basically scarred over and shut itself. Had to be mouth breather ever since! 😑

  21. All the drinking I did in my 20s. I never got to the level where it was a health concern (or even alcoholism, really), but some of the dumbest things I’ve ever done were under the influence of alcohol. I wish I could go back with the perspective that I have now.

  22. I’ve not long turned 40. Didn’t really sort my life out until a little over 3 years ago.

    Made some poor decisions

    Partied into my mid 30s like I was 21

    Was a financial mess

    I don’t regret any of it though. It makes you who you are.

    In 3 years 4 months I’ve become debt free, have savings and a house deposit and I’m stone cold sober the whole time. I never look back on any of it with any regret.

  23. Absolutely destroying my health.

    I’m 368 pounds at 38 years old. It’s insane. I grew up loving martial arts and loving being strong. now my health is absolutely fucked. I’m in week 2 of trying to turn it around and it just seems impossible. Did you know after a few days of eating really good I actually feel SICK if I don’t eat some junk food? It’s true. I woke up yesterday feeling gross and didn’t feel better till I ate some pizza. Nobody believes me.

    I know it’s only week 2. I’m trying. I’m tracking every calorie I eat. I bought a food scale and I’m going to the gym. I bought a bunch of healthy alternative snacks. I’m trying to concentrate on protein and fiber.

    I look in the mirror and I just don’t see it. I don’t see a near 400 pound man. But I’m going to die and I don’t want to.

  24. I had a FWB in my 20s, to whom I wasn’t very kind. It still eats at me. Always be kind.

  25. I had a female best friend and we were both single. We were in a hot tub together and both were a little drunk and she kept dropping subtle hints that she was into me and I didn’t catch on to it. We became distant after I got a girlfriend and I never understood why, but I do now.

    Part of me not noticing or catching on is the fact that she is way above my league, and in turn shows my lack of confidence at the time.

    I have a gorgeous wife now, turns out your personality can make up for the lackluster looks lol

  26. At 19, I had a motorcycle crash. The insurance paid well. My Dad’s friend offered to sell me a great house, all brick, 3 bedroom, 2 baths, with a full, finished basement on about 5 acres. I didn’t buy it, I decided it was too far out of town. I’ve regretted that for decades.

  27. Taking my relationship with my parents for granted. Not calling not coming over for dinner. I thought I was living my own independent life. Now that they are gone I’m truly on my own and would give anything to go back and be a better son.

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