“What’s The Dumbest Thing You’ve Done In Your 20’s?” (85 Answers)


When does someone truly become an adult? In many countries, turning 18 is a turning point in the eyes of the law that unlocks all sorts of privileges. But as this Reddit post will show, many agree that we’ll continue making all sorts of dumb mistakes throughout our early and mid 20s!


The truth is that different people mature at different rates. Furthermore, the question of when you actually become an adult can really vary depending on whether you ask a lawyer, a doctor, a psychologist, or your parents! As you read this list, we invite you to reflect on your own life - when, if ever, do you think you “grew up”?



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


#1

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 credits: Blackbeltchicken


#2

Assumed climbing the corporate ladder is the way to do life

Image credits: Pugwhip


#3

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.

Image credits: Char10


#4

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 credits: badgirlkayy


#5

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 credits: stormscape10x


#6

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 credits: InfamousCelery4438


#7

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

Image credits: MarmateW


#8

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

Image credits: big-bad-bird


#9

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

Image credits: Flaky_Tumbleweed3598


#10

Got married to the wrong woman.


Never get married to someone who isnt sure if they love you. That person is damaged and needs space.

Image credits: ThatsWhatPutinWants


#11

Beg to be loved.

Image credits: SystemNovel7112


#12

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.

Image credits: benderofdemise


#13

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 credits: HabemusAdDomino


#14

Drove 187 miles to drop her a scarf back that she left at my student house.


Didn't even get a thanks. Just an Instagram story of her wearing the scarf out that night.

Image credits: Swioop


#15

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 credits: RedditorWithClass


#16

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 credits: damagedone37


#17

Not making long or medium term plans

Image credits: Kyadagum_Dulgadee


#18

Got depressed. I know it's not in my control but it sure is dumb. 10 prime years of my life wasted because of that stupid f*****g thing. Couldn't study thus no job. Tried, failed. Tried again, failed again. The b***h of it is that there's no reason. It just happened. I was going on about my day and it was as if all the lights inside me went out.


Here's to trying again.

#19

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

Image credits: Ashtar-the-Squid


#20

letting my fears consume me

Image credits: Middle_Post_5558


#21

jumped from an express train going at a speed of nearly 40-45 kmph. No, not a suicide attempt, it's just that the train wasn't supposed to stop at the station I wanted to get off. So I jumped when it entered the station.


Somehow landed on my feet and couldn't believe it, had a smirk, and as soon as I looked in front, there was a policeman with a stick. Never in my life have i seen a policeman at that station. He casually asked me "Did you just jump from that train?". I went blank. He said," ok, come with me, you're going to the station(police)".


Now comes the fun part. It's an early morning and since the police station is within walking distance from the railway station,i am getting escorted by two policemen, one in front and other back, In the middle of both the station is the local market that sets up at the morning. its crowded and everyone is looking at me,some laughing, while police is making way.I lowered my head down and the only thing coming to my mind is "the walk of shame" from GOT.


Nevertheless, after reaching the staion, the policeman informs me that since its saturday, either you pay fine or be in jail till monday when they will produce me in front of judge.Begged a little, spoke in english a little, acted sincered, made sure they knew am well educated and finally the senior guy let me go with a bribe. was seriously disappointed with how a police station actually looks like. Am from India btw.

Image credits: SkinnySam31


#22

Snuck into a construction site and drove a steam roller around for a while… I couldn’t believe they just left the keys in it

#23

Developed a drinking problem in undergrad that evolved into full-blown alcoholism in grad school. Stopped taking care of myself. Went from a 200 pound muscular 6’2” to a 300 pound slob. Got a DUI in my late 20s. Stopped drinking for a bit, then thought I could maybe drink socially again. I could not. Gained 10 more pounds. Thankfully about 2 years ago I stopped drinking, got diagnosed with ADHD and procured the meds associated with it, and am able to unwind with an edible if I need it as opposed to booze. Dropped down to 255 and am back in the gym. I can’t recover what I lost, but I can do my best to make sure it doesn’t happen again.

#24

Dated the wrong people for access to sex. Knew at the time they were problematic and it lead me on a path of a lot of trauma and having the wrong view of the world.



That took a while to dig out of.

Image credits: WouldUKindlyDMBoobs


#25

Got married, followed by the smartest thing I ever did, got divorced.

Image credits: dibberdott


#26

Let myself get overweight

#27

Broke a window with my forehead. Willingly. Don’t ask

Image credits: Navajo__


#28

Not take a year off between highscool and college to figure out exactly what major I want.


I have changed my major like 10 times and now I’m seeing my classmates graduate or move onto med school and I’m just now piecing together what I wanna do.

#29

drove 80 miles an hour through a blizzard to see a band three hours away. hit a patch of black ice and slid right off the interstate into the snow filled ditch. i was lucky a couple of canadians going thru SD saw me and helped pull me out, and that the only thing that broke was my power steering belt.

#30

Took a $12k loan to buy a motorcycle. Didn’t want to pay for comprehensive insurance, bike got stolen 4 months later

Image credits: toyotasquad


#31

Ruined all my early friendships being an out of control drunk. Gave up the ones I had left when I got sober.


Seven years sober in September. It took three years for people to stop calling me to come party. It's been four years since I've talked to anyone that I didn't bump into at a funeral.

#32

Turned 30.


Should have just stayed 29. So stupid.

#33

Literally nothing. And that's the dumbest thing one can do.

Image credits: AnozerFreakInTheMall


#34

I almost got alcohol poisoning in Madrid and about drowned myself in a hotel bathtub. I could have died a real rockstar’s death. Lol

#35

I drove an hour back home from a party with two people in my car while drunk. The edges of my vision were blurred, but I figured if I just focused on what was in front of me, I'd be OK. The road was almost entirely empty, so I was able to drive from point A to point B without distraction, but all it would have taken was one thing to distract or startle me and it could have ended terribly. I never did anything that dumb again.

#36

Got approved for a credit card with a $5500 limit at 19. Oopsie.

#37

I crashed a golf cart at 29. I was so f****d up with road rash, both ankles were rolled and f****d up a one Achilles pretty bad. It took 2 years for one ankle to feel normal again. Still have a bunch of scarring. Have never f****d myself up so bad before. The road rash and treating it all over my body was one of the most painful things I’ve ever dealt with. I am so careful in those things now and honestly just everything in general. Lucky I didn’t hit my head.

Image credits: ochief19


#38

Snowboarded down a double black chute with no helmet into thick fog.

#39

Quit studies after I won $179,000 in a lottery. Partied hard and had 4 girls in the rotation. Fast forward 2 years, I was 40 pounds overweight, bankrupt working at a minimum wage job with 0 girlfriends. I was a B+ student and could have had a decent career.

#40

Slept with my best friends very recent ex, caught feelings and to this day refuse to admit it to anyone. But I regret not doing something about it then, our friendship did and still means the world to me but I still wish I would of moved on that when I had the chance.

#41

decided against contributing to my company's matching 401k. cost me hundreds of thousands of dollars. =(

Image credits: orange_cuse


#42

Ran up $11k worth of credit card debt over about 18 months when I was 25–26. I didn't become debt free until I was 33 and never had an excellent credit score until 36

#43

Getting blackout drunk multiple times. The first should have been enough to make me fix my s**t.

#44

Tried to buy drugs. Female dealer took my money, called the cops and claimed I was robbing her. Went to jail. Lawyer and detective eventually got the dealer to admit she lied. All charges dropped, but lost my career and friends. Very expensive and hard lesson learned.

#45

I got a great job right out of college with a good 401k plan. I spent every extra penny I had tattooing my whole body. Didn’t start putting money away for retirement till my 30s. I estimate my tattoos cost me well over $100k by this point counting for missed out growth that would have happened. Never too late to start saving.

#46

Traumatized myself by getting lost in the wilderness in New Zealand.

#47

Not buy a house. Back in '01-'03 houses in my old neighborhood were selling for $250-350 k. 20 years later they're worth $1.2-1.5 million.

#48

Worked for a s****y employer that paid me minimum wage and treated me horribly from the ages of 20-29. Should have left that job sooner.

#49

Spent too much time thinking about the world’s/country’s issues rather than figuring out how i wanted to make a living.


You always think you have more time until life hits you in the face, and then you realize how much time you actually dont have.

#50

Not using a condom.

#51

Stayed in relationships with people who had 0 respect for me

#52

Took a group of friends on a cross country trip at my expense. i should have listened to my oldest brother and invested the entire sum of money into google stocks and just held onto them forever. I had $21 000 at the time and it would have been worth $55 Million by today.

#53

In 2007 I was living in Santa Maria Zapotitlan in southern Oaxaca (Mexico) helping out a colleague with his PhD research on the archaeology of the Chontal people. After a few weeks the village council asked us to find the source of a stream that flowed from within a mountain, so they could tap into it as a clean water source. They said to start at the back end of a large cave about an hour's hike away. We got to the cave, got to the back of it, and saw two small caves honeycombing into the floor that were just large enough for us to crawl into. We brought several headlamps, dust masks, and chalk. The two of us made our way down these caves, which began honeycombing even more into 3-5 passages per intersection. We drew arrows on the cave walls to help us find our way back. Some parts were large enough to walk through, others narrowed to the point that we had to crawl or shimmy through.


Eventually we lucked out and found a small passage, again enough to crawl down, where we found the stream flowing. Wouldn't you know, we even found some small, intact ceramic disks at the bank of this stream that were used in other contexts to burn incense. The fact that people hundreds or even thousands of years before us did the same thing, and knew where to go given the potential for many dozens of passageways, still blows my mind.


Looking back, there were so many different ways to die and never be found in those caves, and the entire purpose seemed overboard since they could just tap into the stream by running a pipe a hundred feet up the mouth. Ultimately, I suppose we just wanted to survey a cave as archaeologists in the off-chance of finding something.

#54

Stuck with a girl who not only was full of red flags but then proceeded to have kids with her and got married only to have ruined and wasted 13 years of my life were i couldn't have friends lost almost all of my family because they all disliked her 2 face self and basically have only lived my 20s at a factory putting in over time after over time only to remain broke because the person I was with would go on shopping spreads rather than save for our kids future.... my 20s sucked and now that I am in my 30s it doesn't look much better

Image credits: Southern_Brief_115


#55

Continually deny my abilities and skills to be *humble* . after a while i started to believe that i was infact worthless, do nothing be nothing. I hit 30 and it was like a switch went off, I saw everything objectively and turns out I'm a pretty great dude. Turns out mistaking self doubt for humility is a pretty f****d up poison.

#56

Didn’t ask for help when I got in trouble financially.


I was was sucked into payday loans eventually owing thousand got so bad that my payments were more than my wages. Still struggling now but almost there.


Also refusing to pay two debts and getting two CCJs. One was for a payday loan that I felt was unfair and 2nd was for a parking fine. The original payment was .20p i didn’t buy because I thought it was after hours no payment but they changed it to 24hr pay anyway I was there 12min and they wanted £450 for failing to pay. Both cases court agreed with them and forced me to pay.

#57

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.

Image credits: bantai786OP


#58

Went to Italy and forget to eat pizza

#59

Maxed out my 5000 credit card on a girl so she could go to school and not graduate I'm not with anymore for love. Lol. After some years my credit is back over 700 again but I will definitely never do that again. Lol

#60

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

#61

I cringe when I think how reckless somethings I did were


But I remember turning 21 while being stationed in Germany coming back from Iraq and going on leave with some buddies, did some touring around beautiful Europe .


In Prague we got some drinks and the place we were staying at had open access to its roof, we went up and drank and took in the night view until we were drunk and sitting on the ledge with our feet dangling and joking about how loose and wiggly the bricks we were sitting on was (truly loose) and laughing about how stupid it would be to fall and die in a random street in Prague, better than a random path in Iraq !


So dumb looking back now 16 years later , a lot of people would have been so pissed at me lol

#62

Hands down the dumbest thing I've done was sticking with my ex, that eventually clouded my judgement to a point where I turned to crime.


This is going to be long winded, but hear me out.


I met this girl through my younger sister. I was 20 at the time and was studying to become an accountant. We were very happy in the beginning, and my friends and family loved her. I was just as close with her family. She is 2 years younger than I am, and had just finished high school when we met. Fast forward a year till when she started dropping hints about getting engaged. Like I said, we were happy and started discussing it. She started a job in logistical admin and I had a work/study agreement with a big accounting firm in my home town. They didn't pay fantastic, but covered all my tuition fees.


We eventually got engaged on the 31st of December at a party with our families that I arranged with the intention. Everyone was on board, despite our age, because they saw how happy we were. Little did they know whatbwas about to go down.


A few months later we find a place of our own and moved in together. The first 2 months went well.


This is where it goes south. And quickly so. Whenever I started any conversation about planning and saving up for the wedding we would have after my graduation she shuts me down immediately, and starts talking about going out with her friends that I didn't like to go drinking. At the end of the day we do what she wants and we would spend practically our whole paychecks on drinks for her (I was the driver, so I did mot drink whenever we went out). This then forced me to take money out of my savings to cover the rent and food for that month. And this went on for a month or two, until it worstened.


She reconnected with her old crush in month 4 of us living together, and they start spending more time together. At this point I stopped going out with them, as they want to stay out late during work nights, and she started doing cocaine with the guy. Whenever I bring up my issues she turned abusive by verbally and physically assaulting me, threatening to stab me with knives, etc. The last time she did, she broke my nose after repeatedly hammerfisting my face.


My financial troubles set in after I depleted my savings having to pay rent, buy food, and put fuel in my car to drive her and myself to work and back (we worked on opposite ends of town). She never contributed a thing and spent her money on going out and drugs, and I eventually ran out of money, and did not have money for fuel. At this point I am so scared of her, that I don't want to tell her in fear of what she might do next, that I started taking my licence plates off, filling up my car at gas stations and driving away without paying. I did this a few times till I was outed with security footage that was blasted over facebook.


During this whole time I was too afraid to go to my parents asking for help, because of my pride I couldn't swallow. I ended up losing my job and subsequently my studies.


When she found out she ended things with me moved back to her mom. A few days later she came to me and told me that she was pregnant and that it was mine. I took her to the doctor, paid for the visit, the scans, the tests and everything, just for her to turn around and come cleam that it was the high school crush' child after he asked for a paternity test.


They are still together, and I got my life back on track. I finished my studies and am an accountant now, I payed everyone back and they did not press charges after I begged and pleaded. I am married now and couldn't be happier. I just wish I never met her.

#63

I do have a fully functional life but in my twenties i definitely locked out of the door all of those basic experiences one should live at least once in life.


I'm talking about taking an international trip, or going at a concert or trying to get new friends and such. I mostly followed an unreacheable professional dream, which was such because i never intended to move out of my comfort zone in the first place, and then found some refugee and gratification in lonely hobbys i experienced at home.


It took me a huge amount of guts to get out of that pond and start living a bit. Deeper inside i still pay the price of such inaction today, and having professional and family responsibilities now doesn't help.

Image credits: Trollercoaster101


#64

I was 20, there was this bicyclists in the road acting like they were a car. This was durring rush hour and I had an appointment to make.


The guy was just biking in the road. There was a bike lane available, there was sidewalk available.


In our town there is an ordnance that states bicyclists can bike in the road but are treated as vehicles. They are only allowed to bike in the road on roads with a speed limit of 35 or under. This road was a 45.


People in front of me kept passing him and honking their horns. I am behind him and 20 year old me decides to honk his horn.


The guy just turns around while pedaling and flicks me off and I read his lips saying f**k you.


So I pass him using a turn lane and when I'm in front of him a few car lengths I tap the breaks to scare him. Well he wasn't looking and I had to legitimately slow down because of traffic ahead and he ran slap into the back of my car. Flew up on my roof and everything. Damaged his bike


He insisted on calling the police and kept telling me how I was screwed. When the local PD showed up they wrote him a ticket for following too closely and and another for biking on an unpermitted road. Then they told him to stay in the bike lane or on the sidewalk.


So the dumbest thing I did was break check a bicyclists, and probably could have potentially really hurt the guy, but I was not legally responsible because he broke the law.

#65

Faked being depressed often times and eventually got depressed.

#66

Broke up with (what may as well have been) the greatest girlfriend I've ever had. 3 years later I'm still single and I think about her from time to time

#67

Marrying my on again off again when I accidentally got her pregnant. I mean I don’t regret my kids in the least. But that 5 year marriage was the worst time of my life.

#68

Going straight into grad school was such an awful decision for me. I came out of undergrad completely set with no debt, ready to move to the next stage. I really wanted to pivot to a semi-related field, and I graduated in 2020 (R.I.P. job market), so I decided to go and get a master's. I wasted a year and a half of my life, took on tens of thousands in debt, and then dropped out because I realized I hated my new field, and student life was making me extremely depressed

#69

Isolate myself when things got hard

#70

Got engaged to a horse girl.

#71

Didn’t go back to school to improve my grades to go to university to study to become what I really wanted to become.

#72

Got into a half-hearted relationship and wasted 3 years of my life.

#73

Fell into a debilitating drug addiction. I have 26 months sober on the 5th!

#74

Only thing I can think is making 20k in stocks and throwing it all on a make or break deal that didn’t come through, this was pre house and pre kids, money seemed to be much more readily available but once them bills start to appear having spare cash gets harder and harder, that 20k would be very helpful right now, apart from that I’m happy with every decision I’ve made.

#75

Wasted it with the wrong person. Met at 22, married at 25, divorced at 28. My 20s were completely lost to an abusive marriage, 10/10 would not recommend

#76

Turning 21 soon and I can already say the dumbest thing I've done is not working as hard as I should for my uni work.

#77

Thinking that the relationship I was in was going to be forever. Could not be more naive.

#78

Gave up on my 1st marriage. We had problems, and I didn’t know about undiagnosed bi-poler disorder. I know now, and maybe if we had gotten her help things would have been different.


I never got over her completely, and for decades I thought about her all the time. Not everyday, but I’d bet it was at least every week.

#79

turning 24 next month and i know i’ll remember my years from 20-25 for the drugs, alcohol, failed relationships/friendships and my clinical depression/anxiety diagnoses.


my new outlook is trying to give more time to myself and doing what i want to do, how i want to do it, in my own timing!

#80

Lots of random sex, fortunately no pregnancies or infections, but I think I was too risky in practically saying yes to everything

#81

Try to wife up the first girl I dated. Major mistake.

#82

Married the wrong one, had a kid together cause ‘it would make me happy so WE will be happy again’


6 months later ‘I’m still not happy! I want a divorce!”


So 17.5 years of child support - but worth every dime to escape

#83

Not get proper mental health help. I was working full time and trying to go to school and medical stuff was just not on my mind or my budget. I got diagnosed with bipolar at 30 and I think of all that would have been better if I would have been diagnosed earlier. I flunked out of many college classes in my 20s because of cycling mania/depression and I often think if it would have been controlled better or hell, if I would have known even, I would have done better in school and actually have a degree right now.

#84

Not build my credit

#85

I'm in my 20's and really getting addicted in sports betting, guess i should stop while im still in control