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People Reveal Their Biggest Regrets From Their 20s

Woman holding up balloons to celebrate her 24th birthday
Photo by Ana Tavares on Unsplash

Reddit user bigchungusman12 asked: 'What is your biggest regret from your 20s?'

It's reasonable to assume that while a person is growing up, they're going to make some mistakes and even do some things that they'll look back on and wish that they hadn't when they're older.

But one period of time a lot of people find themselves regretting is how they spent their twenties.


The first decade, where we're out on our own while also still figuring things out, is supposed to be one of the highlights of our lives, but it's inevitably filled with mishaps.

Cringing, Redditor bigchungusman12 asked:

"What is your biggest regret from your 20s?"

Unreciprocated Love

"Crossing oceans for people who wouldn’t jump puddles for me."

- thatwasmycupcake

"I feel this one. I've been in many many situations where I put so much into a friendship/relationship and get absolutely nothing in return. Even if it was just comforting someone for weeks at a time then I have something I'm going through and they just so obviously don't give a s**t."

"I never do anything with the expectation of a return, but f*ck if it doesn't hurt when it just becomes obvious people don't care nearly as much about you. I refuse to be someone's convenience. I refuse to be all give EVER again. It's never worth it."

- ThatGodD**nB***h

So Lazy

"I was lazy. I spent the better part of my early 20s just chilling and having fun. That’s great and all, but I was also broke as h**l."

- TazzzTM

"Same, there was a period of about two years where I'd sit at home with no shirt on and either post stupid s**t on the internet or play PlayStation Two. Really just earning money, mowing lawns, whatever, and saving it would've been very beneficial."

- three-sense

Shorter Road To No Contact

"Not getting away from my family. I realized now they're all abusive and toxic and don't give a d**n about anything but themselves. I should have left a long time ago; what a waste of time."

- haseo8998

"Good for you for figuring it out, many people never reach that point and waste more than their 20s."

- IndividualCut4703

Growing A Savings Account

"Not saving ten percent of every paycheck."

- chimara57

"Every dollar was just so valuable. It was hard."

- Cold-Lynx575

"Like how, I am not even able to afford food?"

- Sxpths

"Adding into this, if your work offers 401k, match that s**t and max it out. You are literally leaving free money on the table if you don't because it is in simple terms an investment account that both you and your employer put money into."

"If not offered, take that percentage and put it in a Roth IRA."

"I'm still in my 20's but I'm going to be starting the 30s likely with $50k in investments because of my 'work' that I've done investing with a percentage. Some will laugh at that number and some will sneer at it, but there are too many with $0 in their thirties because they did nothing with investing in adulthood."

"The whole game is time. A million doesn't appear out of thin air, and I don't expect it to happen anytime soon, but time makes it work. Someone with a decent amount of money over a decade of their 20s thrown into safer investments is going to have a much easier time getting to retirement having to put in less monthly than someone that waited until 30s or even later to try to catch up."

"That 10 percent doesn't have to be a 'I'm losing 10 percent of my income,' it can be a mix of, 'I'm considering these benefits, etc., to be my 10 percent.'"

"The first month or two, it was a setback re-budgeting my meager income now that I had 'lost' some of it, but if you can budget appropriately it can be done."

- NOlerct3

Enjoying The Music Scene

"Not seeing more bands. I feel like concert tickets are getting more out of control with prices."

- Big-Adhesiveness3361

"My regret would be that some of the artists either died or got sick/injured and can’t tour anymore."

- Fair_Quote_1255

"Seeing bands is one of the things I don’t regret at all. I used to go out three to four times a week and saw so many future big names when their tickets were 15 to 20 dollars."

"Now I go out twice a year because I’m not spending 80 dollars to see the same quality of emerging artists and spend 15 dollars on well drinks. It’s so much more expensive and you have so much less fun."

- Counterboudd

Not Taking The Leap

"Staying at a dead-end job because I was too scared to pursue my dream career."

- mama2coco

"Well, when you enter the workforce in 2008 (huge housing crash recession), you get it embedded that just having a job is a good thing. Don't risk it for something else."

"Turns out I'd have made more money sooner if I'd have just jumped jobs here and there."

- IdislikeSpiders

Low Self-Esteem

"Low self-esteem and confidence, and the missed opportunities that entailed."

- InbhirNis

"Yep! Wish I knew how awesome I was 10 years ago. I don’t say that to sound egotistical but I have massive self-esteem issues that really held me back."

- ClearMacaroon8675

Poor Education

"Not taking my education seriously, to be honest."

- HandoCalrissian

"Yeah, I'm in my 20s and not doing good in school at the moment. I wish I could turn back time."

- Cool_Juice_4608

"Late 30s here. I finished college this year. Some employers are asking for your GPA. Will anyone go through the trouble to verify it? Doubt it."

"But do yourselves a favor and work hard at school, do it like it’s a job that pays you. Future you will thank you for it."

- JCOII

The Wrong Kind Of Commitment

"Being in a committed relationship with someone I didn’t really like for most of it."

- hwhaleshark

"I'm near the end of my 20s and did exactly this. Only recently met somebody and went, 'Oh, that's what that's supposed to feel like.' Don't do it."

- ricksauce22

"Huuuuuge mistake. I dated a woman which I wasn't compatible with twice, and I regret it so much. Can't explain why other than I was young. I would have been better off and likely more successful earlier if I recognized the situation and got out sooner."

"The silver lining is it all worked out for me but I warn people all the time: Don't stay in a relationship you aren't committed to, don't jump the gun and marry the wrong person."

- Schindlers_Cat

An Unhealthy Journey

"Not finding exercise earlier."

- ElmolovesArchie

"This. Cause if I had, I'd be living with a healthy liver instead of waiting for a transplant. I'm only 55. Take care of your health. It means more than money."

- thumostheos

The Proper Technique

"Lifting with my back instead of my legs."

- 97Minutes

"I'm feeling some of that lower back pain right now."

- RivalCanine

"Ahh the joy of living with a herniated disc."

- miffyvo

Not Seeking Help

"I was mentally ill and refused help and lost 10 years of my life. I hid from the world and like a spectator, I watched my friends and peers be young, go to college, date, travel, get married, and start families while I repeated the same day for 10 years."

"Now it’s my turn. I’m in my 30’s and by some miracle (and extensive treatment) was able to recover my life and personality. And I’ll be d**ned if I waste another second brooding over what might have been."

"'Throw some roses into the abyss and say here is my thanks to the monster that did not succeed in swallowing me alive,' said Nietzsche, for a reason."

- Mickmackal89

Poor Dental Health

"Not taking care of my teeth and not jumping into my current career earlier."

- Jhon_doe_smokes

"Dentist here, it’s pretty unfortunate but the only way we can fix cavities (which is essentially damaged/decayed bone) is via surgical intervention. I hear this all the time, and you wouldn’t believe how many patients I have in their 30s and 40s wearing dentures."

" It can happen to anyone, some people are much more genetically predisposed to tooth decay and get it even with perfect diet/hygiene."

- mountain_guy77

An Important Piece Of Advice

"I spent too much of my twenties taking advice from people whose lives I absolutely did not want."

- Ube_Ape

"Ohhhh, I'm 22, and this is something I'm going to have to think about, because I hadn't heard this one yet."

- DylanBlair699

Avoiding Failure No Matter What

"This comment will probably get buried but I wish I spent more time taking risks and expecting failure."

"I was pretty risk averse in my 20s but looking back, even if I did two years failing and learning and two years at my 20s job (versus four years at my 20s job), I likely would have wound up in around the same place as I am now give or take, likely no worse but also likely better and with more experience of what I do and more importantly do not enjoy."

- JustHereToHangOut


For these Redditors, there were so many things that they would have done differently if they could go back and try again, including investing in their health and wealth early, loving someone else, and taking a few more chances.

Fortunately, the twenties are only one decade, and while it would have been nice to start yesterday what we could do today, they still have a chance to do better now.

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