“What’s The Dumbest Thing You’ve Done In Your 20s?” (20 Answers)

Published 1 year ago

Growing up we realise that there are so many mistakes we made that could have easily been avoided. However, due to stubbornness or lack of maturity, we may have fool-hardily engaged in unhealthy activities that only affect us in our later years. Furthermore, there may be many things we should have done which in hindsight may have made our current quality of life better too.

One Reddit conversation explored these epiphanies that people had far too late in life. Check out some of the answers to the question, “What’s the dumbest thing you’ve done in your 20s?”. It got folks thinking and sharing some of their deepest regrets and mistakes from which we’ve shared a select few below that are especially insightful.

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This question got people to share some of their deepest regrets and mistakes


Image source: Flaky_Tumbleweed3598, MART PRODUCTION

Sold my body for money and allowed myself to be abused and humiliated on nearly a daily basis.


Image source: Blackbeltchicken, Chris F

Drank my way through my entire 20s. After 25 it wasn’t really fun anymore but that didn’t stop me. Drank for another 5 years. My 20s are a total blur splattered with some fun times here and there. But mostly just me running away from things with alcohol. Almost 17 years later and not one drop. My 30s and 40s are exceptionally better.


Image source: RedditorWithClass, Marcus Aurelius

I had good teeth for most of my life, until I fell into a very dark, depressed place in my late teens and early 20s — at which point, I didn’t care about anything, including my teeth. I got the help I needed a couple of years ago and have been doing much better, mentally speaking, since then, and I’ve been taking care of my teeth. I do all the right things: brush twice a day, floss, avoid sugary drinks, etc., but no matter how hard I try to stay on top of them and keep them in good shape, they’re continuing to get worse as I haven’t been able to get the previous damage fixed due to financial reasons (dental work is expensive AF). Moral of the story for anybody reading this: TAKE CARE OF YOUR TEETH, or you WILL regret it!


Image source: badgirlkayy, Jefferson Palomique

Not getting help for my depression sooner. Spent the entire first half of my 20s in the darkest place I can imagine, and all I needed to feel better was some meds once a day


Image source: Ashtar-the-Squid, RDNE Stock project

Not standing up for myself and let other peope walk all over me.


Image source: InfamousCelery4438, cottonbro studio

Whilst partying with some construction guys at my new office building one Friday night, I let them hold me by the ankles, so I could lay flat on the crenelated stone roof opening and admire their handiwork.

Unfortunately, I had my purse on my arm, and my wallet fell out, unbeknownst to me. I’d just come from the store, where I’d cashed my entire paycheck. I was upset all weekend.

Come Monday morning, my supervisor called me into her office. She handed me my wallet and said, “The maintenance guy spotted your wallet on the roof of the parking garage. I don’t want to know how it got there, just don’t ever do that again.”

All the cash was still inside. And I never let construction dudes dangle me from a rooftop again. Nice stonework, though.


Image source: Pugwhip, Dana Tentis

Assumed climbing the corporate ladder is the way to do life


Image source: HabemusAdDomino, Victor Freitas

I took powerlifting way too seriously. I spent 7 years in gyms, for hours every day, skipping every social occasion and holiday. I didn’t get as strong as I wanted to. I just got all sorts of physical issues to deal with for the rest of my life now.


Image source: Char10, MART PRODUCTION

Moved in with a girlfriend before finding out more about her preferences. We had been dating for a year but I didn’t realize how much of a problem she had sharing until we lived together. We did for 5 years and never shared a bedroom, had everything split down the middle including the pantry and fridge, even when it came to spices she insisted on me getting my own. She hated it when I would be in the same room as her unless it was under “her terms.”Whenever I asked to make our relationship more of a shared experience I was gaslit into believing I was wrong for not allowing boundaries. She moved out a month ago and I couldn’t believe how quickly my mental health improved simply by not having that toxic influence around anymore.


Let myself get overweight

Image source: teaching-man


Image source: SystemNovel7112, Priscilla Du Preez

Beg to be loved.


Went to Italy and forget to eat pizza

Image source: TheStraightishGuy


Image source: MarmateW, Oladimeji Ajegbile

Not studying properly.

At the time studying for 2-7 years seemed like a life time, but now at 30 I wish I had done it. Don’t have the money or flexibility to do it now


Turned 30.

Should have just stayed 29. So stupid.

Image source: Blue_Bomber27


Image source: big-bad-bird, cottonbro studio

Worked way too hard and burnt out. Sacrificed family time. Sacrificed health. Need to pace yourself at the age of 20-30.


Image source: stormscape10x, Alex Green

Everyone wants to hear about dumb stuff like driving eight hours to get with someone you liked only for it to end up being a booty call. However, I personally think it was my general lack of effort to build any good habits like exercise. Your body likes routines, and my routine of gaming for 15 hours a day was not one I should have cultivated.


Image source: damagedone37, energepic.com

Drink and drive.

A lot.

Never got busted. Quite stupid. I am now 5 years sober(unrelated). I say this from the bottom of my heart. There are friends, taxis, Uber, Lyft etc….utilize these for yourself.


Image source: bantai786OP, Alexey Demidov

ones me and my friends nicked a politician’s car just out of curiosity of what’s gonna happen and boy’o boy a lot happened

edit- so we broke one side mirror of the car while it was parked in open ground (also surrounded by 10 other cars) there were no guards nearby but the car started blinking its lights and the boys were just laughing when all of a sudden there were 10 guys with ar riffles with a jacked dude as their head guard surrounding us

I thought they were gonna call the cops but they didn’t, they took us to the security area and the first question the guy asked: “Who sent you ?” we were kinda freaked out but one of us answered “It was by accident” a guard came ahead and smacked his face. he was the toughest dude among all of but that day he almost started crying. this made me freak out a little more, The guard who had smacked one of the boys turned towards me and asked, “What do you have to say for yourself?” I stammered and tried to explain that we were just fooling around and that it was an accident. But the guard wasn’t having any of it. He looked at me with a steely gaze and said, “You guys messed with the wrong people”, well not exactly that coz I translate it

As he spoke, I noticed a sense of fear in his eyes. It was almost as if he was afraid of what his superiors would do if he didn’t handle us properly. I couldn’t blame him. We had clearly broken the rules, and we were in a lot of trouble. they started checking out pockets for knives or any other damaging items, we didn’t had any so that made the situation a little lighter they made us sit there for about 3 hours and also confiscated our phones so there was no chance we could call anyone. we were still freaked out but still chuckling when looking at each other. when it was time for the politician to leave then the head guard finally spoke. “You’re lucky we’re feeling generous today. We’re going to let you go only if you join the rally to lift the hoardings”. it was not so strange request as they usually have to hire men for that work, With that, we were out of the security area the head guard proved all 4 of us with 4 flags we were feeling shaken and humiliated. soon there was a mob of about 200 people which gave an easy way to lose the guards. A group of 15 or so people started an argument over which group will be with the leader’s car but the argument turned into a fight. It couldn’t have been a better time to escape so that’s what we did. the security camp still had our phones so next we went there or rather I went there coz rest of em didn’t seem to care about their phones, the camp had a guard who didn’t recognise me for some reason. I told him that there was a brawl going on at the rally ground and they are calling the guards. That poor soul believed me and went straight to the ground, I couldn’t believe he didn’t even think twice, so I took the phones and also a lighter which was lying there(coz why not ) the boys were on the highway next to the ground (they couldn’t see us coz of the mob) I located them by complete luck. Our car was parked on the other side of the highway so that was also an easy escape for us

As we drove away, I couldn’t help but think about the consequences of our actions. We had put ourselves in a dangerous situation, and we were lucky to have gotten away It was a lesson I would never forget.


Grand of you to think that I stopped doing dumb things after my 20s!

Image source: SpiritedSeries5187


Image source: benderofdemise, Handy Wicaksono

I wanted to say so many things but i read someone forgot to eat pizza in Italy. All of a sudden my dumbest thing wasn’t so dumb, it even cured my depression.

Shanilou Perera

Shanilou has always loved reading and learning about the world we live in. While she enjoys fictional books and stories just as much, since childhood she was especially fascinated by encyclopaedias and strangely enough, self-help books. As a kid, she spent most of her time consuming as much knowledge as she could get her hands on and could always be found at the library. Now, she still enjoys finding out about all the amazing things that surround us in our day-to-day lives and is blessed to be able to write about them to share with the whole world as a profession.

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20s mistakes, biggest mistakes, deepest regrets, dumbest mistakes, hindsight, regrets
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