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Article created by: Rugilė Žemaitytė
Many people enjoy boasting about having zero regrets and standing by every decision they’ve ever made. And while dwelling on the past can be harmful, is it really so bad to reflect on our lives and wish we had done just a few things differently? 

Redditors over 40 have been opening up about the biggest regrets they have from their youth, so we’ve gathered some of their thoughts below. Whether they wish they had started a skincare routine sooner or feel that they missed out on valuable time with their parents, we appreciate their honesty. Enjoy reading through and reflecting on your own choices, and be sure to upvote the replies that remind you not to make the same mistakes!

#1

Elderly couple with grandchildren sharing a moment, illustrating people who are 27 and over sharing their biggest regrets. Not asking older family members more questions about our family and forebears while they were still alive.

PeggyNoNotThatOne , cottonbro Report

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    #2

    Woman with floral shirt reflecting in mirror, symbolizing people who are 27 and over sharing their biggest regrets. Caring too much about what others thought of me.

    Asexualhipposloth , taylor_smith Report

    #3

    Couple in wedding attire holding a bouquet, representing people who are 27 and over sharing biggest regrets. Thinking I needed a romantic partner to be happy. I stayed in an abusive marriage for so long because I couldn’t imagine doing things alone. It is infinitely better to be alone than in a bad relationship. When I choose to be in a relationship again, it will be because I’m happy and compatible with the person, not because I don’t want to be alone.

    anitabelle , nate_dumlao Report

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    #4

    Two people over 27 having a deep conversation over coffee, sharing life regrets and lessons learned. Not setting firm boundaries with people. Givers have to set limits because takers have no limits.

    log899 , priscilladupreez Report

    #5

    Young woman over 27 reflecting on regrets while sitting alone at a dimly lit bar with empty wine glasses nearby. Not enjoying being single. Looking back my social interactions were centered around finding the one. I should have just enjoyed getting to know people

    atx_buffalos , cottonbro Report

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    #6

    Person with a yellow backpack hiking through a green mountain valley, reflecting on regrets from people who are 27 and over. I should've started traveling much earlier in life, while i was still young & fit. That & not taking better care of my teeth

    thrwawaythrwaway_now , hollymandarich Report

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    #7

    Person over 27 holding a credit card and using a laptop to share biggest regrets and lessons learned online Not saving money is a big one. The younger you are simple things like a dollar a day, or 10-20 etc in an account that you don’t withdrawal from.

    JackSkelllington , liza-summer Report

    #8

    Person over 27 applying sunscreen on arm under clear blue sky, reflecting self-care and life lessons from regrets. Seems so cliche but I did not wear enough sunscreen. I used to do the whole lay out with baby oil so I could get a "savage" tan. How stupid. Now my face looks like a topographic map of California. Wear sunscreen kids!

    Catalyst886 , mikhail-nilov Report

    #9

    Group of people over 27 enjoying outdoors, reflecting on life and sharing biggest regrets to learn from mistakes. Not enjoying it more , didn't realize how fast my younger years would pass

    mugshade1 , wildlittlethingsphoto Report

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    #10

    Woman raising arms in a city street at night, representing people 27 and over sharing their biggest regrets. Living life on other people’s terms, and not mine. Young people: it’s YOUR life. YOU are entitled to live it the way YOU want. ❤️

    trashleybanks , cys_escapes Report

    #11

    Young woman practicing yoga outdoors, symbolizing mindfulness and reflection for people who are 27 and over regrets. Stretching and maintaining muscle mass. When I had kids I stopped both and it took a decade to get that back. Treat your body well. Something happens around 38 and the better shape you are in the better your 40’s and after will feel.

    katelynn2380210 , lulusphotography Report

    #12

    Person over 27 holding a mirror reflecting their face, sitting by a window in a dimly lit room, reflecting on regrets. Not appreciating how lovely I was

    marvellousmim82 , chemrain Report

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    #13

    Close-up of orange foam earplugs scattered together, representing people over 27 sharing their biggest regrets. Shoulda worn ear plugs at all of those concerts...

    jer123456and7 , quinnanya Report

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    #14

    Woman with curly black hair sitting with arms crossed, reflecting on regrets shared by people 27 and over. Worrying so much. In hindsight all that stuff seem so silly now.

    Hattkake , enginakyurt Report

    #15

    Hand holding a lit cigarette with smoke rising against a blurred background representing regrets of people 27 and over. Smoking for several years! Waste of money and not good for the health

    takechances2024 , minhtit96 Report

    #16

    Close-up of a person playing electric guitar, symbolizing lessons from people who are 27 and over sharing regrets. Not learning a musical instrument. I’m trying now but it’s harder at my ancient age.

    loves-science , freestocks Report

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    #17

    Man sharing advice with a teenage boy outdoors, illustrating people who are 27 and over sharing their biggest regrets. Trusting authority figures and older adults above my own instinct on things.

    ifnotmewh0 , kindelmedia Report

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    #18

    Three salt-rimmed shots with lemon wedges, illustrating people over 27 reflecting on their biggest regrets and lessons learned. Spending most of my 20s drunk. I don't regret all the fun, because it was great fun. But I could have had that same fun without being so wasted. I kicked it in my early 30s, don't miss it.

    SouthTippBass , iam_os Report

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    #19

    Person taking notes on a clipboard while talking with another individual during a casual meeting about regrets and life lessons. Not getting the mental health assistance I desperately needed. I've suffered from anxiety and mild depression since my teen years. In part, it made me a recluse and a social outcast because I felt I was unable to interact properly with people and the world. Today, on meds, I am a different person. I no longer fear social interactions, and if I was aware of the results back when I was a teen, I likely would have made better decisions for myself.

    ZephyrShow , alex-green Report

    #20

    Two young adults outdoors, sharing a moment that reflects on regrets from people who are 27 and over. Spending too much time worrying about love and not enough time concentrating on happiness.

    UsesCommonSense , trinitykubassek Report

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    #21

    Two people over 27 having a thoughtful conversation outdoors, sharing life regrets and lessons learned. **Deferring too readily to the judgment of others.** I had the naive belief that other people had my best interest at heart. Speak up for yourself. Defend your own decisions. No one is out there waiting to make you a star.

    Gorf_the_Magnificent , priscilladupreez Report

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    #22

    Two young men over 27 sitting outdoors appearing regretful, reflecting on life lessons and shared mistakes. Dating/being friends with losers and feeling responsible for them.

    Hollocene13 , s_kawee Report

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    #23

    Person over 27 using a payment terminal, highlighting common regrets and lessons shared by people aged 27 and over. Not being careful with my credit. I got my first credit card at 18 and went absolutely crazy. It’s taken me years to climb up to decent credit and even more years to get to excellent credit.

    BlackBra81 , karolina-grabowska Report

    #24

    Hand pressing buttons on an ATM keypad, symbolizing people 27 and over sharing their biggest regrets to learn from. Not saving for my retirement as soon as I got a job when I was 18, started at 25. I’m 43 now, won’t retire until I’m closer to 70

    Trin_42 , eduschadesoares Report

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    #25

    Group of people aged 27 and over sharing moments and learning from their biggest regrets outdoors on a sunny day. Not investing and not appreciating people who love you.

    PermissionCrazy8452 , kampus Report

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    #26

    Two women aged 27 and over sharing their biggest regrets during an evening conversation outdoors. Speaking too quick not listening and thinking more.

    Brave_Bluebird5042 , kxvn_lx Report

    #27

    Young person over 27 with headphones on, writing notes near a laptop, reflecting on life regrets and lessons. Not going harder at everything, thinking I had time. You dont.

    duraace206 , soundtrap Report

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