Anyone who is past the age of 30 will have at least one “young and dumb” moment that will keep their face locked in a cringe for a good few minutes every time they remember it. These regrettable decisions could include vices they experimented with, ill-advised romantic choices, or financial moves that carry long-term repercussions.
You will find a lot of these themes in the following stories you’re about to read. These are candid accounts of women on Reddit who recall the headshake-inducing times of their youth. Just by reading, you can tell some of these still sting today.
Many of these stories may involve sensitive topics, so proceed with caution. And if you feel like sharing your own experiences, feel free to do so in the comments.
#1
40s but I can tell you in my 20s I genuinely tried way too hard to be liked by people I never ever see or hear from anymore. It doesn’t matter what anyone thinks, be comfortable with yourself.
Image source: vaultie66, Marina Piano (not the actual photo)
#2
The people I mistreated.
Image source: CurrentSingleStatus, Getty Images (not the actual photo)
#3
Giving someone a second chance when I already knew the first chance was a mistake.
Image source: Honest-Band-4766, A. C. (not the actual photo)
#4
Running up $6,000 in credit card debit on stupid stuff. Took me forever to pay that off and I don’t even want to know how much extra I paid in interest.
Image source: Taycotar, Vitaly Gariev (not the actual photo)
#5
The amount of times I was in situations that horrify me looking back as an adult because I wasn’t taught to say “no” when I was uncomfortable.
Image source: Useful-Leg-9861, Getty Images (not the actual photo)
#6
Dating a 30 year-old when I was 18. Now that I’m in my 30’s, I look at 18 year-olds and realize that dude was a creep and a loser.
Image source: Ill_Gene_187, Mindy Sabiston (not the actual photo)
#7
I still can’t get over the fact that I didn’t do a year abroad in uni because of a boyfriend.
Image source: p_r_d_v_a, Clay Banks (not the actual photo)
#8
Not reporting my attacker because he said I’d be the third report of SA against him, sending him to jail. He said it’d be my fault if he went.
Image source: OkPerformancer, Curated Lifestyle (not the actual photo)
#9
Getting in the tanning bed in college. Can’t retin-A away that no matter how hard I try!
Image source: Radiant-Laugh-6519, Boris Hamer (not the actual photo)
#10
CIGARETTES, they had a hold on me from 18-25 until I got pregnant.
Image source: Fickle_Ostrich2466, Juan Encalada (not the actual photo)
#11
Getting s**t faced at a bar to the point where I lost all my friends. Got lost sat on a curb and thankfully was picked up by a group of other girls that got me an uber and sent me home. Only to realize I didn’t have keys to get into my apartment. Only friend that picked up was a guy and I slept in their basement. Then they had to take me home the next morning when my roommate was able to let me in. Idk so many moments for things to go badly. Glad it didn’t. But I was stupid and would d*e if I heard my niece or daughter was doing s**t like that .
Image source: solarnuggets, Elena Helade (not the actual photo)
#12
Not knowing my worth sooner and sticking it out in some pretty awful relationships. I shouldn’t have stayed as long as I did. I lost years of my life. I’m gaining them back now though!
Image source: Icy-Safe-3098, Getty Images (not the actual photo)
#13
People pleasing and pouring everything into everyone but myself. Don’t do it.
Image source: Front-Efficiency-805, Vince Fleming (not the actual photo)
#14
I wish I had stayed single for most of my young adult life. I would have saved a lot of money and time, and been better off in the long run.
Image source: dessipants, Priscilla Du Preez (not the actual photo)
#15
Letting him get away with hitting me.
Image source: Itisjustme2112, https://kaboompics.com/ (not the actual photo)
#16
Having a child with the wrong man. I made a lot of excuses for his behavior towards me and it ended with my child seeing things I can’t take back. Trust your gut.
Image source: Heartburnbaby03, Helena Lopes (not the actual photo)
#17
I went on a date with my professor.
Image source: Momomeow91, cottonbro studio (not the actual photo)
#18
Not going to therapy sooner. Would have changed my life.
Image source: snugginator, MART PRODUCTION (not the actual photo)
#19
Dating my s****y ex for years. Not finding my current partner sooner. I know that last one sounds ridiculous but about a year ago my current partner and I realized that we were always *this close* to meeting. He worked for a while at the theatre my Dad and I went to every Sunday. My cousin and his friends were both members of this music co-op. Just lots of little things like that.
Image source: Ghost_Popcorn, Vitaly Gariev (not the actual photo)
#20
While living abroad I met someone, let my guard down, and we fell for each other quickly – texting all day long, travelling, and taking long weekend trips, etc.
I had no idea he had gotten his ex pregnant (before we met) and they were planning on moving her to the same country to raise their baby together. One day, he stopped texting me back until I demanded a response and that’s when he sent a picture of his baby boy.
Don’t recommend.
Image source: PossiblyBored, Ivan S (not the actual photo)
#21
I went to Ozzfest when I was like 12 in a f*****g bikini top and shorts.
Image source: Asmodeuss323, Globelet Reusable (not the actual photo)
#22
Should have taken the time to think before getting married.
Image source: Sensitive_Coffee7742, Patrick Langwallner (not the actual photo)
#23
Not learning about financial literacy and setting myself up for success with a solid career. Was a super artsy teenager, attempted an English degree after graduating highschool, dropped out and worked in hospitality/service for way longer then I should have with the thought that as long as I was working things were fine because I had a job that could “support” my hobby (writing). Am now early thirties going back to school for nursing and wish I had just done it at some point in my twenties instead.
Image source: Fayble, Alexander Grey (not the actual photo)
#24
Staying with someone for most of my 20s that gave all the red flags. He even kissed a supposed friend within the first few months of us being together in front of me at the nightclub, but I still stuck by him because of “love”.
Many issues turned out continued to happen but because he was my first proper love, I felt like I deserved it and this was how things were meant to be.
Turns out… I didn’t deserve any of that. I still deal with elements of trust issues and require assurance which I’ve worked through via therapy, but the insecurity still haunts me.
Image source: Extreme-Target-8413, Hrant Khachatryan (not the actual photo)
#25
Getting married at 20 ( I should add I am 60ish and it still haunts me !!!).
Image source: cmwulf, Getty Images (not the actual photo)
#26
Dating a married man who claimed to be in an open marriage.
Image source: LoanEarly5813, Priscilla Du Preez (not the actual photo)
#27
Some of if not ALL the one night stands I’ve ever had.
Image source: Legitimate-Pie-5218, Getty Images (not the actual photo)
#28
Not appreciating my body more. I was so obsessed with being thinner and prettier and everything in between. I’m now in my 30s and wish I had realized how great I was and talked more positively to myself.
Lessons learned and even though I’m heavier now than my 30s, I’m loving what my body can do and focusing on feeling healthy and confident rather than trying to be someone I’m not.
Image source: shenlyism, Natalia Blauth (not the actual photo)
#29
How I spelt my kid’s middle name. It’s soooo cringe, I’ve actually apologized to her she loves it, thinks it’s unique and cool, but I d*e inside whenever I have to write it on anything.
Image source: 1thruZero, Fellipe Ditadi (not the actual photo)
#30
Dating a guy who didn’t want me to move 2 hours down south to get a 150% salary increase because he was afraid of me out earning him, also didn’t want to move with me, also didn’t want to marry me. And then kept dating him long distance for 3 more years after that.
Image source: Ok_Jello_2441, Curated Lifestyle (not the actual photo)
#31
Not being open to dating and normal social life. I grew up in a more conservative country and moving to the US I adapted super well except for this part of my life. It took me way too long to date, and now at 40s while I’m very successful and have built a wonderful life, I’m single and likely will never partner up.
Image source: annatwork
#32
Not trusting my gut. I was easily influenced and grew up being a people pleaser. It led to a bunch of crossroads in my life where I knew I should have went one way, but due to external pressure I went the other way. I had a hard time standing up for myself.
I don’t think about what could have been because it truly makes me sick. Everything from my career to homes to relationships has been impacted.
Now that I’m almost 40, I love my life and where I ended up but I spent most of my 20s and 30s regretting major life decisions.
Image source: lexi8251
#33
Not being emotionally smarter. Every time I had an issue with a friend, I’d just cut them out of my life instead of trying to work things out.
Image source: Almost_Mira
#34
Every guy I dated longer than 2 years lmao.
Image source: ImplementFunny66
#35
Keeping me up until 3:00AM is a bit of an exaggeration, but I think about this pretty often.
My very first job out of college was at a pretty prestigious finance firm in a big city. I had no idea how to be professional or what I wanted to do when I “grew up” and being in that world with so much wealth was overwhelming.
At one point I decided to study for the LSAT and just see how things went. One of the CEO’s saw me studying and offered to have the company “help” with school. I didn’t know what the meant and a few months later I just quit and found another job. I realized much later that he was offering for the company to pay for my school. I could have just…stayed and got a free law degree when I was young and living in a big city and had very few other obligations.
Maybe law school wasn’t my journey, but it could have helped me figure out what that journey might have been. In hindsight it seems so silly to not just “do it for free”. I’m lucky to not have many regrets in my life, but this one sticks with me a bit.
Image source: Soulah
#36
Oh and attending the university I went to. I had a 4.0 GPA with volunteer work, excellent LORs, an exceptional SAT score, and years of extracurriculars. I ended up choosing a school whose medium accepted GPA was 2.1. There was no research opportunities (something I really need now that Im trying to get into grad school), it was a dry, commuter campus. No parties, in a rural community, with people who thought Paramore was edgy. I should hve transferred but I had convinced myself that that was the equivalent to dropping out entirely for whatever reason. Just an overall awful experience.
Image source: Ghost_Popcorn
#37
1. Blocked out s****l a***e. Guess who still has unresolved intimacy issues, whoop whoop.
2. Racking up lots of debt. I still can’t fathom why oh why younger me?
Image source: Mental-Law-1851
#38
I regret not putting myself out there more. In my early 40s feeling so behind because I’ve barely done anything.
Image source: True_Beginning_9699
#39
That my ex didn’t give back all my stuff and still owns me money.
Image source: Vanillachestnut
#40
Walking home from a night out with my bestie, and we hear Oasis coming from a block of apartments. We start singing along, they notice, and a half dozen nice boys we’d never met before invited us up to drink with them. We did. First thing I did on arriving was slug someone else’s open drink.
Ladies, **DO NOT DO THIS**. In another universe we were cut into tiny pieces and never seen again!
Image source: ibiacmbyww
#41
I would walk everywhere. Downtown. Alone. Late at night. No phone. Almost every day.
Image source: ahumblecardamompod
#42
The dudes I wasted my time with
The male friends who were just a**holes to me in the name of jokes. The guys I dated who were unkind to me that I took because I thought I loved them.
Image source: Individual_Physics29
#43
Giving up moving abroad because i wanted to stay with my boyfriend who left me to move abroad 6 months later.
Image source: Professional-Door954
#44
Getting married and having kids with the first and only man I’ve ever dated. Love my kids but hate solo parenting.
Image source: Halloween_Barbie
#45
Didn’t follow my own instincts. Continued to push through something I knew I couldn’t do bc it thought I wouldn’t be able to support myself if I took time to heal. I should have waited, used available financial resources, gotten my health sorted out, before it bit me in the a*s and led me to a career failure, and finally physical disability. Take care of your emotional and physical self!
Image source: Hamsterlee
#46
Marrying someone and staying married once I found out that they were a bully.
He was and still is a bully.
Image source: travelwithmedear
#47
It was 2018. I was drunk on the banks of the Hudson River. It was dark and I don’t remember much… except I lost my beautiful one-of-a-kind alpaca fur hat (no alpacas were harmed) that I had gotten from the Union Square Holiday Market a couple years prior.
I think about that hat every year.. I’ve tried to look up the vendors I’ve tried contacting Etsy creators… it’s just gone.
Image source: noreasonnorrhyme
#48
Credit card debt.
Image source: Educational-Cow-5989
#49
Devoting too much energy to dating.
Image source: The_Long_Lady
#50
Dating older men.
Image source: Acceptable_Song1401
#51
40s – Got married at 19, divorced at 27. Took on far too much responsibility and left a shell of myself.
I should have spent more time alone, had fun and put myself first.
Image source: OoooSecrety
#52
While at the beach I asked a guy If he could give me a ride in his boat, he did. I got a ride home from the bar from randoms.
I invited a guy I met at the bar back to my place. And then the big bad night. I had c*****e and went to a bar with who I thought was a friend and potential bf, he took my phone battery and keys for my apartment, I think I was d*****d cause the last thing I remember is flashes of me walking to my apartment, couldn’t find my keys, back of the building, and then waking up on a pile of snow with a cut on my hip…
I went back to the bar cause I was so confused, it was 3am and the owner was locking up and I asked him for help. I told him where my ex bf lived and he was thankfully a good guy and got me there, my ex bf called the cops and they met us at my place and the 2 guys I was with at the bar were in my place unplugging the tv and xbox. So ya pretty sure I finally got to my 9th life and that was the night I stopped drinking and it’s been 12 years since I’ve had a drink.
Another regret is giving my body away because I thought guys liked s*x so if I have s*x with them they’ll like me.. that’s not true and you lose a part of yourself when you do that. Have fun but be safe!
Image source: NarwhalEmergency9391
#53
I’m 41 and just threw some water at a non-aggressive wasp nest to make sure they were still in there. Guess who just got stung? Will probably still be haunting me at 3 am. Never too old to make stupid decisions!
Image source: squeakiecritter
#54
See the red flags and completely ignoring them. 🚩🚩🚩.
Image source: Itisjustme2112
#55
Thinking going out with people to bars in college would make me lifelong friends.
Image source: Zealousideal-Owl-283
#56
Dating a close friends ex boyfriend. I was so stupid and excited about getting attention from a cute guy, I totally neglected my friend and her feelings. Dumb mistake I made at 20. Never again!!!
Image source: Throwawaysei95
#57
Leaving out of anger and disappointment in the middle of a fight with my boyfriend. Drove around for 15 minutes, came home and he had k****d himself.
Image source: Disastrous-Fudge-391
#58
Looking for love over learning about myself. So much time on wasted trying to be loved by losers instead of loving me.
Image source: Chloebebe13
#59
When I got so belligerent my freshman year of college I woke up in a giant field, climbed a fence in the dark, fell off said fence and smacked my head on the concrete. Walked two miles in the wrong direction and ended up at a McDonald’s a ways from campus. The area I went to school is known for human trafficking. I still can’t believe I did that/ came out with nothing but a bad hangover….
Image source: meowzermama
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