People Reveal Their Biggest Regrets in Life

August 21, 2018 | Delaney Caulfield

People Reveal Their Biggest Regrets in Life

“I'd rather regret the things I've done than regret the things I haven't done.”—Lucille Ball.

“Do not brood over your past mistakes and failures as this will only fill your mind with grief, regret, and depression. Do not repeat them in the future.”—Swami Sivananda.

We all have moments that we look back on and wish we had made a different choice. They pop into our brain and agonize us when we can’t sleep at night. They cast a shadow on an otherwise well-lived life. We can never get these moments back, we’ll never be able to relive them and get to experience a different outcome. Instead, they will play over and over again in our minds. A perverse torture we never move beyond, to our therapists’ constant disappointment, no doubt. They come in all sizes, little and big, and they don’t discriminate.

Regrets are hauntings by past decisions that we would all do well to shake free from or conduct some sort of hypnosis to block out the memory forever. But for all the embarrassment, frustration and anxiety they cause us we wouldn’t be the people we are today without having experienced them in the first place. They help us grow and serve as a reminder of how far we’ve come. Here are some of the biggest regrets that Redditors have in their lives—but, fortunately for many of us, there’s still time! We can all learn a little from these stories and maybe not make the same mistakes.

Biggest Regrets factsHuffPost

42. A Child Mourns

My mother passed away when I was eight years old. Cancer. It came to the point where death was inevitable. My dad asked if I wanted to see her and I said no.

Biggest Regrets factsTickWallpaper

41. Dear Teens: Heed These Words

I was painfully shy and awkward around strangers and the opposite sex when I was in elementary school and high school. I really presumed that I had so few friends because I wasn't the kind of person other people liked. I also presumed my social awkwardness was inherent and something I was completely unable to overcome.

I only found out that both of those are untrue when I was, like, 30. I kind of wish I had my teen years back so I could force myself out of that awkward shell and enjoy my youth a bit more.

Biggest Regrets factsThe Ross Center

40. Grief is a Bad Dream You Can’t Wake Up From

Three years ago my father passed away. In the months leading up to his death, he had been struggling with idiopathic pulmonary fibrosis—his lungs were turning to scar tissue and no one knew why—and had been working with Duke Medical Center exploring the possibility of a lung transplant. He had just returned home from a multi-day battery of tests and examinations there and was feeling pretty good about his chances when he fell ill with what appeared to be pneumonia and was hospitalized. He was having difficulty breathing (well, more than usual) so he was put on a ventilator.

Very late the previous night I had returned to my own home, about an hour from the hospital, after a long car trip and was still tired from the journey when I received a call from my mother explaining the situation. We agreed I'd visit the next day when they had more information on his condition and he'd had a chance to settle in.

That evening his doctors decided to put him into (what was meant to be) a temporary drug-induced coma; he was fighting the ventilator and in a lot of pain, and putting him under would give his body a chance to rest and hopefully heal as the machine did his breathing for him. A few days later he was airlifted from the local hospital back to Duke Medical, where he was reevaluated as a transplant candidate. His application was rejected because his condition had deteriorated so far that the transplant board didn't believe he'd be able to survive the procedure or the months of rehabilitation that would follow.

We made the decision to put him out of his misery and take him off life support, and my mother and brother and I watched him pass away. Our decision ended up being validated by how quickly his body gave out; it took less than five minutes for him to go. The staff didn't even have time to bring us snacks.

Did you know that hospitals provide cookies, crackers, soda, etc. to the families of patients waiting to die? I didn't. We thought it was kind of funny, even at the time, but the nurses explained it usually took hours for someone to pass on after life support was shut off, and those waiting usually got hungry.

Two things bothered me about the manner of his passing. One was personal, and what I consider my greatest regret even though I strive to live a life free of them: I didn't make the effort to go visit him the day he was hospitalized. I hadn't known it at the time, of course—no one did—but it would have been my last chance to speak to him. The second was a sort of outrage on his behalf: he had been full of hope about getting his disease permanently managed and returning to some semblance of a normal life, but he got sick; then he was put under with the assurance it was just temporary, and he'd be woken back up in a few days—I took lots of pictures of him getting wheeled out and loaded into the chopper, to show him the adventure he'd been on without knowing once he woke back up—but he never woke back up. It hurt that I didn't get to say goodbye, but it hurt much more that he didn't get to say his goodbyes, to anyone. It took me a long time to get over that.

That night, after his body was taken away for cremation, my now-smaller family returned to our nearby hotel suite and I slept on the sofa in the main room, letting my mother and younger brother take the bed. In my dreams—and I rarely dream—there had been some kind of mistake; my father came to the door of our hotel room and laughed at how inept the hospital had been, mixing him up with someone else, now go help your mother pack so we can go home. I woke up and stared at the ceiling of the hotel room and everything felt wrong for a while until I was able to sort out the difference between dream and reality once more.

Biggest Regrets factsAboutIslam

39. Never Heard That One Before

I'm only 20 but I regret spending my childhood reading books instead of joining sports. I feel like sports would have helped me socially and physically so much.


Biggest Regrets factsWaterford Institute

38. Youthful Take-Backs

Hanging out with a friend instead of visiting my father in the hospital. He died that night and I never got to say goodbye.

Biggest Regrets factsOdyssey

37. Moments of Weakness

I yelled at my grandma for complaining about something—I don't remember what it was, something stupid—because I was tired and it was cold and after midnight on a day I had to wake up early to go teach kindergarten and she was sick.

I woke up 2 hours early to my mother crying so hard I could hear her across the house. My grandmother died about 2 hours after I yelled at her. I still haven't forgiven myself for it and I'm not sure I ever will.

Biggest Regrets factsDr. Jennifer Thomas

36. Who Could Have Known

Selling all my bitcoins when they hit $10.

Biggest Regrets factsBloomberg

35. Conforming to Societal Norms Means No One Wins

I'm 31. My biggest regret is saying yes to a marriage proposal when I was 23 that caused me to waste a good part of my 20s engaged to someone who I knew wasn't a good match in the first place. I did this heavily because of family and outside pressure.

Biggest Regrets factsVIX

34. You Never Stop Learning

Not paying enough attention in high school. I barely passed and didn't actually learn much of anything. Going to really regret that one.

Biggest Regrets factsGifted Challenges

33. Self Reflection is Growth

I've got plenty of regrets but I'll share my most recent one: Not treating my girlfriend better. I see now that I didn't appreciate her enough, I really didn't trust her enough. There are so many times where I wish I could take back something, kept my trap shut etc., etc. I'm torturing myself.

I go over and over in my head what I wish happened instead. I loved her with all my heart and I still do but she's left me. I’m a wreck right now, I'm extremely unhappy and wish so many things in my life were different. I don't know what to do. Or rather, where to start.

Biggest Regrets factsIndependent

32. It Pays to Remember Every Action Has a Consequence

I'm 35. I spent the latter part of my high school life doing too much partying and ended up selling drugs which ended up derailing me from my plans for college and a career. I ended up getting in trouble with the law and getting trapped in the system. I did two stints in prison as a result of my mistakes and have only been out and well since the end of 2009. Now I have to navigate the world with a criminal record, which includes two drug felonies.

I never really thought about the consequences of my actions while I was screwing up and honestly was in such a strange state that I didn't think about living long enough to deal with my mistakes.

Now I am in a good place in life with a wonderful wife whom I love more than anything. I have mended all of the bridges that I burned during my madness and life is good but those mistakes I made when I was younger will never go away.

Biggest Regrets factsCinnamon Solar

31. When One Door Closes

Dropping out of a full-ride scholarship engineering program to become a full-time pothead working with kids. Things have changed, now I’m in the field without the degree so it all worked out. I’m getting the same pay as if I graduated the school.


Biggest Regrets factsThe Modern Man

30. Career Choices Are Hard

I'm 28. I wish I had developed a more concrete plan for my career earlier. I sort of had this strange assumption that if you get a degree from a respectable college it would make numerous avenues of employment available to me.

I'm trying to break into a field that has nothing to do with my degree and I have no relevant internships either. It's a serious barrier to overcome despite some reasonably impressive credentials I have obtained outside of college.

Biggest Regrets factsPro-Essay-Writer

29. Marriage Isn't for the Uncertain

I'm 30. I got married at 21. I really wish I'd had the courage to break up with him before we got married. Instead, I walked out a year after the wedding. I'm sure he hates me now but if he knew how disastrous my love life was for eight years after, he might get some peace.

From the alcoholic who almost hit me that one time, an older man, to the washed-up wannabe musician who lied about his height to the second older guy who wanted to be with me but couldn't handle it but did I want to move to Australia anyway?

I have somehow ended up in a healthy, loving relationship, but darn, I have some seriously bad romantic decisions I regret.


Biggest Regrets factsBlikk

28. An Important Lesson to Learn

(Then age 22, now 29) Loaning an ex $10,000. He cheated and never paid me back.

I learned the valuable lesson to never loan money you can't afford to lose.

Biggest Regrets factsStartsmile

27. Extremely Relatable

Jumping into college right after high school. I had no freaking idea who I was or what I wanted to do.

A lot of money wasted, drugs consumed, and destructive relationships later, I kind of know what I want and who I am…kind of.

Biggest Regrets factsEden Village Church

26. You’re Ready When You’re Ready

I'm 26. I didn't properly develop my social skills until a few years ago and I only lost my virginity this summer. I wish both would have happened at least ten years earlier. Would have saved me a lot of frustrations and disappointments.

Biggest Regrets factsSteemit

25. The Night Shift Is Damaging But so Is Comparing Yourself to Others

Started working night shift when I was 20. I am 24 now and finally got a new Monday to Friday day job. But nights have already done their damage, I am shy, reclusive, don't go out much, been single for nearly five years now, don't know how to talk to girls anymore when I am out, don't know how to make new friends. Now my best friends are having kids and I am getting worried that soon I will be on my own completely.

Biggest Regrets factsYouthmanual

24. So Many Regrets

I’m 25 and here are a few.

Not going back to see my grandfather before he died.

The self-destructive things I did when I was a teenager.

Not trying harder when I was in school.

Ruining a bunch of my relationships.


Biggest Regrets factsWallpaperMaiden

23. That’s a Big One

Not fulfilling my potential.

Biggest Regrets factsHarvard Business Review

22. So Naive, So Full of Life

I'm 23. Young enough to do what I want...but I have been thinking that since 18. I have nothing to show for those five years that flew by and I had some huge aspirations that I was sure to have conquered by now.

Biggest Regrets factsIntegrative Psychology Services

21. Lessons From Our Elders

Not talking to my grandfather about his experiences in World War II before he passed.

Biggest Regrets factsUPPSolutions

20. Cherish Those Around You

An ex of mine. It’s a long story, but she still haunts my dreams. While we don't talk anymore, we did clear the water a couple of years ago and I got closure, mostly. So I'm not going crazy over her, but a part of me will always miss her. She's a hole in my heart that I carry proudly, as weird as that sounds.

I'd like to add, as I totally missed the point of the question, was that I regret the way the relationship went, and not her. She's the best thing that ever happened to me, and I'll never forget her.

Biggest Regrets factsSoha

19. Sow Those Oats People

Not sleeping with more people while I still had the chance. I'm 31 and married.

Biggest Regrets factsEarnest

18. Math is a Wonderful Thing

Not studying math properly in school. Turns out, it's the only thing that matters in this world.

Biggest Regrets factsYouTube

17. It Would Be So Practical Now

Not getting a degree in one of the STEM streams all those years ago. Playing catch up now. :(

Biggest Regrets factsWrike

16. I Still Don’t Know What I’m Good At

Not knowing what I'm really good at and want to pursue earlier in my life.

Also, finding out that I have ADHD earlier in life.

Biggest Regrets factsTerve

15. School Is Not For Fools!

I was 16 at the time of my mistake, I’m 21 now.

Dropping out of high school...twice. I got good grades. School was easy as heck for me, so easy, I thought I could do better on my own. I was wrong. I dropped out after sophomore year, then again after junior year. Both times I tried homeschooling myself and seriously lacked the motivation. Eventually, I just decided to get my GED and move on. I left school at 16 years old and didn't return ‘til I was 20.

It was the biggest mistake of my life so far. It affected everything. I lost my friends. I lost everything that I thought I was going to improve on and get more of. I didn't get smarter—in actuality, I feel I am less intelligent than I was at 16—five years of smoking pot could be why though.

I can attribute most of my failures and shortcomings to a seemingly easy decision to stop going to school. I was accepted to Simon's Rock College of Bard, an early college for high school students who feel unchallenged, at 16. I feel like I couldn't even get accepted again now that I'm 21. That haunts me every day.

I'm getting my stuff together now, kinda, but I've lost so much. I hope one day I can get back on track to where I would have been, but now I have a daughter and soon a I don't know. Every day I look up and realize how much potential I've lost. I could be in an Ivy League school. I could be making six figures in two years, whereas now I will just be transferring to an engineering school—hopefully—in a year or so.

Biggest Regrets factsYouTube

14. Always Be Safe

Not wearing a condom—even though I knew the girl got around a little bit—and contracting genital herpes. Now I have to share my herpes with my wife and she lived a perfectly safe sexual past. I wish she didn't have to deal with it, it's my cross to bear.

Biggest Regrets factsGet It Online Durban

13. Sports Are Fun

I honestly and truly wish I had the drive/someone to push me in football. I love the game but football was really lax at my high school and I was a big/fat kid that was used for my size, not because I tried. When I went to college I realized how much I would have loved to play college football but because I never tried in high school, there was no way.

Biggest Regrets factsOffice of the Vice President for Research

12. No Regrets

Age 25. I don't regret anything. Everything that has happened or I have done has led me to be the person I am now and I like who I am now. It's taken a long time to like myself but I'm finally there.

Biggest Regrets factsPillowfights

11. Debt is a Constant Regret

Going to a private university instead of a public one, and not sticking to my original degree in engineering. Stupid me ends up with $150K in debt and a degree that is nearly useless.

Biggest Regrets factsMoney Sustainability

10. Always Care About Your Health

I wish I started caring about my weight much sooner. I've lost some good people because they gave up waiting around and I don't blame them at all.

Biggest Regrets factsHabibi Halaqas

9. Defeated By Society

This will be long and I doubt anyone will see it. I don't care because this is actually for me. I haven't thought about it in a long time and want the memories today. Besides, it beats working.

I regret letting myself lose touch with the first person I loved who loved me back after I was forced to move away. She was a keystone in my life though we were together for a short time and I’m probably just a short meaningless moment in her life.

Like most of us, I was an awkward kid. A huge nerd who was too smart for his own good and that just made it even harder to form relationships at all let alone with girls. I had been hanging out with a bad crowd and knew I should get new friends before I got in too deep.

I was also an honors student so I didn't fit in well with my misfit friends either. They didn’t like me. I didn’t like them. They kept me around to be the butt of all their jokes and generally treat badly. Like I said, I was awkward as heck and my only two real friends lived an hour away from me. If I was lucky, I would see them for a weekend or two each month.

During the school week, I was on my own. I was the perfect blend of huge nerd and a want-to-be heavy metal kid with a lot of Dungeons and Dragons mixed in. I was tall and lanky—probably 130 pounds soaking wet. During, my freshman year of high school I spent my lunches alone reading fantasy novels in the library. There is even a picture of it in my freshman yearbook: Just me sitting alone reading a David Eddings book sporting a mullet and wearing a grey cardigan sweater with a white turtleneck underneath. Oh, and the type of metal wire glasses you see 65-year-old businessmen wearing. The ones with really big lenses the cover most of your face.

I’m in that yearbook photo with a caption about me reading in the library at lunch. Something I longed for each day just to get away. The yearbook itself is crisp and clean. It still looks brand new 20-something years later—not a single signature inside it because I had no friends and knew that anyone who would want to sign it would only write something mean.

One of the misfit kids was a close friend, who treated me differently when the rest of the gang wasn’t around, but he was from a tough background and even then I knew he was headed in a bad direction. We hung out a lot that summer. He was good looking and good girls were always falling for his bad boy charm. In spite of my awkwardness, I could pick up on social clues.

I decided that summer I would cut my hair, ask for new clothes and contacts in spite of us being very poor and try to conform to what I saw other kids doing at least in appearance. I knew that people do judge a book by its cover and I didn’t learn that at lunch in the library. I saw it as a huge defeat to myself, but I was tired of being alone. I still remember asking my father for different clothes and contacts. I had to tell him I was a freak that everyone ridiculed and that I was embarrassed by myself. I could tell he understood even though he thought the world of his son.

Biggest Regrets factsZikorah

8. Don’t Get in Your Own Way

Letting the most beautiful girls I have ever met slip past me because of self-doubt and social awkwardness. Once when I was 17 and again when I was 20. The worst part is the fact that both times it was girls in which we really got along and were really into each other.

Biggest Regrets factsThese days I call myself a runner...

7. Education is Highly Valued By Employers

I'm 31. For me, dropping out of high school and not going to college is my biggest regret. When you are young you tend not—at least I didn't—to appreciate how much more difficult this can make your life.

Biggest Regrets factsZero To Alpha

6. Accepting Yourself Is Hard

Not being myself. I waited until this year to finally admit to myself that I am bisexual. I tried so hard to make myself into someone I wasn't all these years, feel like I wasted my 20s and my life is still so complicated and messed up. Oh, also a furry by the way. I’m 33 years old now.

Biggest Regrets factsCaylor Solutions

5. Inner Truths

A female friend in college revealed she had a crush on me and had for a long while. She was probably my best friend at the time and I never caught on to this because I'm super gay, and at the time I was super deep in the closet.

She broke down and revealed this one night after we had grabbed dinner and saw a movie—I honestly can't believe I never caught on. I did the only thing I could do, since this was clearly hurting her, and I told her I was gay. She said she had started to suspect that a while ago, but wasn't sure and decided to pursue me anyways.

And this is where I become scared: That night was the last time I saw her. I closed myself off slowly. Stopped responded to Facebook, texts, calls, everything. She was the first person I had told I was gay, and I was not ready for it. She was fine with it though—so fine with it that I think she tried setting me up with her brother at one point, but I was not fine with it at all.

I was so nervous back then about everything, I wanted no one to know I was gay because of this overwhelming sense of dread I had about it, and suddenly someone knew my biggest secret and I couldn't stand it. I got scared, so scared I cut her off completely within a few months.

I still feel bad about it, and I should because it wasn't a good thing to do. I've thought about reconciling a few times, but she's left the state now, moved on with her life, and from what I can tell is a very different person from when I knew her. I'm out now, and finally happy with myself and my life, but this thing I did to a good friend weighs on me.


Biggest Regrets factsOdyssey

4. Live in the Slow Lane

The day my dad killed himself, I was walking out of the house and running late for class. He asked me to have some breakfast with him but I just yelled out, "I don't have time," and walked out.

Biggest Regrets factsCarnisseria Can Pepito

3. Don't Give up


Attempting suicide. I don't talk about this much, but screw it. I'm 34.

Trigger warning. This might not be an easy read for some of you.

This is the first time I've ever opened up about any of this in public. Even my family isn't really aware of a lot of this, for reasons I'm sure you're about to understand.

My first time, in a word, was due to bullying.

I was an awkward teenager, and I've got a very Norwegian name that looks like someone ate a bunch of alphabet soup, shot diarrhea of it at a wall, and wrote down the result. I got messed with quite a bit as a result of both facts, ended up being shuttled around between schools because I'd inevitably get kicked out of a school for fighting over it. After a certain point, I snapped. Stalked around my high school breaking stuff, did a few grand worth of damage. They had to call my parents to come grab me, and I was institutionalized for about six months at 16 years of age. I put on a good face, did my time in the hospital, and finally got released. Less than three days later I was in the ICU after a massive overdose of my psych meds. I had to have my stomach pumped, got charcoal, it was a pretty close call. For the record? Having charcoal pumped into your stomach through a tube in your nose isn't really a pleasant experience.

I just got to a point where I felt like the cycle wouldn't end. I'd never graduate, I'd always be miserable, and I'd started having the usual effects of PTSD. Hallucinations, self-destructive thoughts about how terrible I was, scary rages that left me exhausted and cost me a lot of beloved possessions. Panic attacks.

After a few weeks, I got out of ICU and back into the hospital. About a year later, give or take, I was finally out and sent from New York to Colorado, to stay with my dad. If it's because the state said I had to, or if my mother couldn't take looking at me after all that, I'll probably never really know.

Fast forward about 14 years, my marriage dissolved and my PTSD was still mostly untreated. I'd been homeless off and on the entire time, scraping by with odd jobs and teaching MMA to keep myself alive. I kicked off a wicked drug habit that culminated in a pretty sick addiction. I did a lot of things I'm not proud of, and that weighs on you.

To make a long story short, I finally cut that stuff out of my life, and moved back in with my parents to regain some semblance of normalcy. Had enough. Got a job, probably the best I'd ever had to that point. And then I lost it because of the stress of finally treating my disease. I spun out, with PTSD it's a pretty tough fight to keep depression in check unless you've got some serious tools to control it. I started feeling the urge to pick up my old habits, and again just kinda felt like it was going to be more of the same. So, I hit that point again. Gave up. Overdosed. This one didn't go as badly, I was only in the hospital for about a month, and actually got some skills to actually keep it in check.

Since, I've traveled all over America. I started in Maine and found my way all the way out to Montana. Started writing, which worked out better than I'd expect, all things considered. But you know what? I can't say it ever really gets better. Things are stable, but medical care is expensive and I'm still paying the bills for getting put back together again. My last attempt was probably about 3-4 years ago, it left me with thousands in debt. But, things are a bit different now. I've gotten so close to death that I coulda had a nice chat with her, overdosed so badly that I lost control of my bodily functions and almost coded a few times. I know what it's like, and I know how bad of an idea it is.

What people never tell you, and what I'm going to, is that when you get that close? All you can think about is how much of a mistake you're making. It's painful, it's humiliating, and it's ugly. I still flashback to being on the table and having my clothes cut off. Vomiting charcoal, and later pooping it out in one painful brick. They never talk about the look in your family's eyes. My mom came to see me in the hospital while they were putting me together, I will never forget the look of fear in her eyes. Me stuck to a table, covered in tubes and wires and beeping machines.

Strapped down to prevent injuring myself in case I had a seizure. Black rock flowing down my throat. In more pain than I'd ever experience before or since. One lesson I did take away from it is exactly how mean and selfish the entire act is. What I never considered was exactly how bad it was going to hurt my family, that probably hurt more than almost dying. I still have trouble forming relationships as a result.

Moral of the story is, after having gone through it, and a recurrence, I'm incredibly mellow now. I know how much worse it can be, so nothing phases me. But, I won't lie to you and tell you that the world gets better, or that I got some huge epiphany out of it. My only epiphany is that suicide is really stupid. Life's still hard, that won't ever change. Sometimes I wish I could say some happy platitude about how much more I appreciate every day, but I'd be lying if I said it was the case. You adjust, you move on. My life's probably similar to everyone reading this, it's still just as raw and ugly and real. But, it's also exactly as fun and beautiful and crazy. And I'm still around to live it, so I guess that's a plus.

I'll definitely say that it's the one thing in my entire life that, if I had it to do over, I'd change.

Biggest Regrets factsBody for Wife

2. The Things We Wish We Could Change

I'm 28 and what I regret most is not killing the guy that assaulted my girlfriend.

He was my best friend in high school, but he had messed up views about women. If they dress a certain way they deserve it. If they flirt with you they owe you. That kinda thing.

She told me months after the fact that he attacked her while I was away for a few days. It took every bit of control to not track him down and kill him then. But I knew she needed me there with her more than anything else.

When I confronted him, I screamed, and I was so mad I cried the entire time. But I never hit him. I knew if I did I wouldn't stop until the cops pulled me off of him.

I took the high road and looking back, it makes me feel like a coward. I should have done something. ANYTHING. But all I did was talk.

Almost a decade later, she and I are still together, and we've both gotten our treatments. She's almost all better now, back to normal. I still have major trust issues. I haven't made a new friend since I confronted him, and I've cut almost all ties with the few I had at the time. I just can't bring myself to do it.

Biggest Regrets factsDem Con Watch Blog

1. You Can't Go Back


I should never have kissed my ex-wife on Labor Day 1997. It was the worst decision of my life. I wish I would have just told her to screw off and said I had no interest in talking to her at all. She was a virus that destroyed me and consumed my will to live. Then she moved on. That is the only thing I wish I could make not happen in my life. Not failing to save my father’s life or the abuse from my childhood, just her. I regret everything about her.

Biggest Regrets factsPower of Positivity

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