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.
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#21
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.
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.
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#22
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.
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.
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#23
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 .
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#24
I went on a date with my professor.
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#25
Should have taken the time to think before getting married.
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#26
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.
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#27
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.
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.
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#28
Getting married at 20 ( I should add I am 60ish and it still haunts me !!!).
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#29
Dating a married man who claimed to be in an open marriage.
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#30
Some of if not ALL the one night stands I’ve ever had.
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#31
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.
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#32
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.
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#33
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.
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#35
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.
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#37
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.
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.
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#38
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.
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#39
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?
2. Racking up lots of debt. I still can't fathom why oh why younger me?
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#40
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!
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!
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