Big Mistakes And Even Bigger Regrets

April 13, 2023 | Violet Newbury

Big Mistakes And Even Bigger Regrets

Have you ever wanted to go back in time and change your mind? We all have. Some moments are more cringeworthy than others, while some leave us with lasting feelings of regret. If we could only turn back the clock and undo some of our most trying moments, where would we be now? These Redditors have come forward with the wisdom they've earned the hard way, and some of it is downright heartbreaking.

1. Prescription For Health

I regret not listening to my doctor’s warnings and properly taking care of my diabetes because, let me tell you, this illness has turned my life into a waking nightmare. Since last year, I've had an operation to restore vision in my right eye, one to do the same in my left, as well as an operation to reattach the retina in my left eye. I am currently waiting to have even more surgery.

Basically, I was completely blind for two months. This whole debacle could have been avoided if I wasn't so relaxed about my illness. The regret is real.

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2.  In A Split Second

In my unfenced yard, I've always let my dogs roam freely without a leash. And when they were out there, I never left them alone. I was always with them. It was never an issue...until it was. One of my dogs began roaming further and further when he went outside, especially when I wasn’t paying attention. I will admit it happened much more often than it should have.

Then one day, my worst fears came true...I saw a car hurtling down the street and started frantically calling for my dog. But it was already too late. I regret calling him at all. He was in the neighbour’s yard and probably would have been ok had I not called him. But I did. I watched in horror as someone hit my dog and drove away without stopping.

I held him in my arms as he bled out. My mom drove us as fast as she could to the vet I worked at, but I’m certain he was gone before we even made it into the car. It is my greatest regret in life, and three years later I still can’t stop crying when I think about it. I loved that dog like my son and I can never forgive myself.

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3.  A Forever Love

I dated a boy for years that I will call "Sam". I loved him like crazy. But let me tell you, I made one huge mistake, and it's ruined my life forever. Here's how it happened...Our relationship had ups and downs, but like any young love, the good times were just SO GOOD. He was somehow good at everything. He came from a family that loved and supported him, and to top it off, he had good looks, charisma, and brains.

Man, this kid had the smarts. Everything about him just "fit" for me. We went to a military school together for my last two years of high school and my first two years of college, before asked me to marry him. It wasn’t a big, formal thing-- just a "hey, you know we're going to get married, right?" But because we were young, nothing went as planned.

I thought hard about it, and eventually told him "yes" a few days later. He gave me his class ring. I just couldn't see my life with anyone other than him. But when we wound up going to different colleges, everything changed, and eventually, we broke it off. He wanted to try the world on for size and see what was out there.

It broke my heart, but I agreed. I'm a painfully logical person, and his decision tore me apart, but I didn't want to make him stay and have him resent me for never having felt like he got to "live". If it was meant to be, it would be meant to be, right? I tried to move on. A couple of years passed. I casually dated a bit, and finally wound up moving in with somebody after college.

My heart wasn't in it. Nobody was Sam. I couldn't see a future with this guy I shared a home with, or anyone else I had dated, even though they were all wonderful people. I kept trying to figure out what was wrong with me, and called myself an idiot for being so hung up on my high school sweetheart. I never thought I'd hear from Sam again, but then one day, the unexpected happened.

One night, while my boyfriend was away, Sam called. He had switched majors and it had taken him a couple of years longer than me to graduate. He got his degree in electrical engineering and had this amazing job working for the Navy out in California.  He told me everything was so much clearer to him now. He had "lived" and didn't care for it.

He had had other women and partied his heart out, but what he truly wanted was a life with me. He said he had made the wrong choice and asked if I would take him back and give him another shot. It was everything I had ever wanted to hear from him—a dream come true...But even so, there was still one thing holding me back.

I believed in fidelity, even though I was in a relationship with someone I didn't love. All I wanted to do was tell Sam that I loved him and that we could go slow and give it a shot, because he was "the one" for me. He was the guy. But I couldn't do that, because I was with someone else and I respected him, even if I didn't love him. I wish I could go back and change my answer.

I told Sam that I was glad to hear from him, but that all I could offer him for now was my sincere friendship. We talked for hours. I started to look at other apartments and think of how I could gracefully and kindly break up with the man I lived with. I wasn't going to tell Sam, "Hey, hold up while I break up with this guy, and then I'm yours". I owed the man I lived with more than that.

One night, Sam called again. He asked me again if I would be with him. Everything in me wanted to say "yes" but instead I told him that I would always be his friend, as that's all I could offer while I was with someone else. He told me he loved me. He told me how special I was and would always be to him. He wished me luck, happiness, and good things, and then, he told me goodbye. I told him that I preferred "until next time". I had no idea that this was the last time I'd hear his voice.

When he said goodbye, I didn't know he meant forever. He hung up, drove out into the desert, and took his life. He had a love letter with him that I'd written to him while we were together. He wrote one note to me, one to his parents, and he left me a ring. When I read his note to me, I fell apart. It was utterly devastating.

It read: "I love you. I'm so sorry for not trusting in our love. It's my only regret. Do not follow my weak example. You are strong and beautiful, and a blessing to this world. Until next time". He had saved every note, every letter, and every token of affection that I had ever written or given to him over the years. I regret that I wasn't honest. I regret not telling "Sam" how much I loved him.

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4.  Eye-Opener

I was working in a hot kitchen with a tandoor. I was slapping a piece of Naan into it when some hot flour flew into my eyelashes and burned them off, like, I had ZERO eyelashes left. I looked like a complete fool just because I hadn’t bothered to take off my mascara from the night before. If I have one golden nugget of wisdom, it's this: For the love of all that is holy—wash off your makeup no matter what.

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5.  Just One Of The Mean Girls

Second through fifth grade was the worst, but middle school was not much better. To give you an idea of how bad it was, I changed schools five times over the course of elementary and middle school. Things improved in the sixth grade. I felt like I was in middle school now, and I could change my image, stay in the background, and not be noticed as much.

I was terrified of making things bad again. We had a free period where you sat around did homework, and just hung out.  We were divided into groups of four. My little group was three very nerdy boys and I actually really enjoyed hanging out with them. They would play a game that was similar to Dungeons and Dragons, but it was imaginary.

They included me and we'd have a very good time. This was just that one period.  Outside of that time, I didn't associate with them because they were known as being weird and nerdy.  So, my biggest regret to this day happened during lunch. I had a couple of good female friends that I would eat with. I had just met these girls and wanted to make a good impression

A few months prior, I had been eating my lunch alone in the bathroom or library. The three boys were in my normal lunch spot with the girls, and they're waving at me.  The girls just made a remark and asked if I knew them. My response was so shameful—I'll never forget it: I just said "no" and we sat somewhere else. I can't explain how heavy this has sat on my heart all these years.

Those boys were nothing but sweet to me, and they just wanted to hang out at lunch, and here I was pretending not to know them. Their faces absolutely dropped when I walked away. I will never be able to forgive myself for that terrible thing. That one mistake completely changed me. After middle school, I finally stopped caring what other people thought of me. I'm nerdy now and proud of it.

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6. Sibling Rivalry

When I was in the eighth grade, I saw my sixth-grade brother walking down the hallway towards me. I body-slammed him as hard as I could into the wall. He limped away, ducked into an empty classroom, and started crying. I wasn’t a violent kid and in general, was a pretty good big brother. Afterward, I felt so bad and I had no idea why I did it. I still apologize for it more than 15 years later. It haunts me that I did something so unnecessary and cruel to my own brother.

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7. In Need

I was going on a camping trip with my dad and I had saved up money to buy snacks and fun stuff for the trip. The grocery store was right next to the dollar store, and an old man with a walker came up to the car and asked if he could have a dollar for food.  He asked for a dollar, so I guess that's why I only handed him a dollar.

I came out of the grocery store with a load of snacks, but when I spotted the old man, my heart dropped. He walked out of the dollar store with a single can of soup. It was the saddest thing ever. I regret not having handed him more money. He bought one meal and I spent my money on a bunch of junk food. It still bothers me ten years later.

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8. Pack Your Bags

Not studying abroad when I had the chance. My boyfriend at the time convinced me not to and I agreed. We were high school sweethearts and had talked about marriage. He hinted at the fact that if I went abroad, our relationship probably wouldn't survive the long distance. I was scared of breaking up so I didn't go. Big regrets. I could have had the experience of a lifetime.


9. A Guilty Conscience

I cheated on my wife as a way to force my decision to get a divorce. It was cowardly and shameful. Although getting divorced was the right decision, my way of doing it was horrible.  I am ashamed of it every day of my life. I constantly live in fear that my son will one day find out. I never even told my now ex-wife. I couldn't look her in the eye for years.

I cried after I cheated on my wife. We were in a sexless marriage for over five years at that point. I realized that I didn't actually want to be intimate with another person. I wanted to have a physical and emotional connection with my wife. The thought of cheating on another partner now makes me physically ill. I would never do something like that ever again.

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10. Computer Error

One of my only true regrets was skipping the last day of my computer class. I skipped out the whole last day of high school, which also meant missing that class. It didn’t seem like a big deal at the time, but our class was small, and we were all really close as it was a two year commitment. We had many inside jokes, serious study hours, and certification tests together.

We were a dorky little family that loved to talk computers and video games. My teacher was hurt that I skipped out, and I’ve regretted it to this day. He was a bit older, so I’m not sure if he’s still around. I wish I could go back, and have spent that last day with everyone, as it truly was the end of a formative chapter of my life.

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11. Bar Hopping

I was on a first date with a girl and we didn't hit it off well at all. We were at a local dive bar having some drinks. She was nice, but the conversation wasn't interesting to me, and I wasn't attracted to her either. The date clearly wasn't going anywhere, but we were having an enjoyable time. There were two older attractive women dancing by themselves, and having a great time while I was having drinks with this girl.

My date went to the bathroom and I went to the bar to get a couple of drinks. While there, one of the older ladies came up to me and tells me, "We're celebrating my birthday tonight and we're going to another bar. Want to join us? We have a taxi outside". I wanted to go so bad, but I couldn't do it. 20 years later and I still think about that night.

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12. Get Rich Quick

It was the 80s when the news was full of stories of "bedroom coders" getting rich writing ZX Spectrum games. So, I decided to drop out of education and spend a year or two writing games. Of course, that's not exactly how it went. Instead, I spent two years playing video games, before finally getting a job in a garage. Eventually, I got on the very bottom rung of IT. It took me until my 40s to get to where I could have been in my 20s. Stay in school kids. Stay in school.

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13. Lost Time

My dad passed when I was 18 and before that, I was "too cool" to hang out with him much. I regret it so much now. He passed from kidney failure after 20+ years with a heart transplant. I ended up needing a heart transplant two years after his passing and had no one that could relate to what I was going through. That's when the regrets started piling up even more.

I never talked much about his transplant with him. He never came to my high school graduation cause he was working, so he never really got to see me accomplish anything in life. Even though I spent time with him as a kid, as a teen I was too immature to realize the importance of father/son bonding. I wish I could hang out with him. In fact, I miss him every day.

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14.  Birthday Bungle

I had a birthday party at age seven or eight. After my birthday was winding down, I asked one of my dad's friends if he got me anything for my birthday. I was thanking everyone and wanted to make sure I thanked him and didn’t leave him out. He turned beet red and a look of raw embarrassment crossed his face. He mumbled "no" apologetically. I still feel terrible for asking and putting him on the spot.

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15. Incognito

There's this game I play in public places that’s called "the Pat Johnson". Essentially, you go up to someone who looks nothing like you, and tell them they look like Pat Johnson. When they ask who that is, you say "I'm Pat Johnson". I did this to a random guy, but eventually became friends with him. Here's where the regret comes in: The problem is, he still thinks I'm Pat Johnson.

I now have to pretend that that's my name whenever I see him. It's the biggest lie I've ever been caught in.

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16. A Painful Reminder

Rolling up my car windows that one time.  I got home from work and it started raining. I ran out to roll up my car's windows.  I slipped and fell. No big deal right? Wrong. Unbeknownst to me, I had just severely pinched both sciatic nerves and there is nothing anyone can do to fix it. Since I was 18, I am in pain all the time.

I haven't slept for more than six hours at once in 22 years. I can't sit in one position for more than an hour or so. It takes away all my motivation and makes doing things I want to do impossible sometimes. It has shaped so many aspects of my life and has changed me as a person. I actually don't remember what it feels like to not be in pain. Screw those stupid car windows.

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17. Market Madness

I must have been 16 or 17, and was driving in the City Market parking lot. I was getting ready to park when I saw a shopping cart. I decided to push it with my car for a moment, then stop and see it roll on it's own. This was a BIG (and very expensive) mistake. I bashed the shopping cart up against a parked car. My friends were in the car and were not enthused. The embarrassment was real.

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18. Nothing To Smile About

Not taking better care of my teeth. I'm now 36 and require some serious work. I am terrified of what the verdict will be when I go in. Dentures, or worse I think. I often think about what I would give to reset the clock and have nice white straight teeth. The idea of having that is so foreign to me. Never wanting to smile, always hiding behind a mustache, it's the only part of my life that really causes me stress on a daily basis.

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19. A Difficult Destiny

I used to play Destiny with a group of guys who I only knew through the game. The major parts people play are specific long missions that require a lot of teamwork and in some cases, leadership to get the loot. Everyone has to know what he or she is doing, because if one person messes up then everybody in the game dies.

I usually take on the role of leader when teaching new players and even just playing normally because I thought I was good at it. Over time, I stopped playing because everybody else stopped as well. A few years later, one of my old buddies that I would play with turns up in an Xbox party chat with me and we catch up.

I ask him, "Hey, I never asked but we never play Destiny anymore. What's up with that?" His response was a smack in the face: "I'm gonna be honest, we kept playing. You were just REALLY unpleasant and nobody wanted to be in a lobby with you... Sorry man. " I immediately felt insulted but after a few seconds realized exactly what he meant.

If one person would mess up, even if it was a common mistake, I would scream and scream at them until they felt terrible. I would give everyone a hard time, while making excuses for my own mistakes. I stopped doing that so quickly, that the personality shift was noticeable to all my friends. I regret being difficult, but without that moment of realization, I wouldn't have improved as a person.

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20. Hide and Seek

When I was around 11 years old, my mom took us to JCPenny. I was bored and playing under the racks. I noticed a woman had left her keys on a stack of clothing and walked away. She was gone for a while. I kept looking at those keys and got the bright idea to hide them. So I did. Right as we were leaving, there was a woman running around panicked, looking for her keys. I was one evil kid cause I didn’t say a word and left with my mom.

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21. Man’s Best Friend

When I was younger my parents let us adopt our dog, and I didn’t treat her very well, even though I begged to get her. I barely played with her and got annoyed taking her on walks. I’d pull the leash really hard so she had to come the way I wanted, to the point my mom threatened to bring her back because of my negligence.

I left my dog for three years to go to school and when I came back, she still accepted me. I’m now 23 and my dog is pushing 16.  I feel like she lived this long for me to finally have a good relationship with her. She’s deaf now, barks all the time, and wears diapers, but I try to make sure she has the best possible life while she has time.

I won’t ever be able to pay back the love she’s shown me unconditionally. I just hope somewhere in her mind she’s forgiven me and that she knows I love her as well. Not a day goes by where I don’t wish I had more time with her to show her the love and affection she always deserved.

Biggest Regrets FactsPixabay

22. All Work, No Play

I've spent my whole life prioritizing my career over my personal life and health, and boy am I paying for it. I’m now 37 and painfully single. I have no kids, and have been diagnosed with a chronic illness that probably manifested due from constant work-related stress and pressure. But that's not even the worst part.

I am also living with my parents. All of my friends have abandoned me, and I’m completely alone. At this age, I always thought I would be married and have children. Every day I think I should have put more effort into taking care of my relationships, and myself instead of giving every ounce of energy I had into "making it big in NYC" and being successful.

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23. The Touch Of A Hand

I regret something that I didn’t do the last time I saw my father. I remember being 11 years old and sitting in a chair on the other side of the room, while my father, who was paralyzed from brain cancer and on the verge of passing, lay in his bed in a palliative care home. My mother and my brother were holding his hands when my mother asked me if I wanted to come over and hold his hand as well.

I just couldn’t. I was crying in the chair hoping for a miracle, but I couldn’t accept that this was my father’s destiny. A couple of minutes later, we left.  He passed a couple of days later. Looking back I regret so much that I didn’t go over to his bedside and just hold his hand. Just so he would know that his kid would be all right.

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24. A Daughter’s Shame

One thing I always think about and regret is the way I treated my mom after she got her knee replacement surgery years ago. I was around 17 or 18 when my mom finally came home after being in the hospital for a few days after her operation. She was obviously in a lot of pain. She needed a lot of help with pretty much everything, even the small things like walking to the bathroom and getting on the bed.

Being the narcissistic teen I was, I thought this was the most annoying thing ever. I thought she was overreacting, and it couldn't have been that bad.  It was an inconvenience to my time. Man, I was so dumb.  One moment I think about in particular is the time she asked me to help her out of the shower because she had a hard time lifting her leg over the tub.

I was so fed up by this point that I stormed over there and just yanked her leg up quickly and dropped it on the other side. I remember her crying from pain. She literally cried in front of me right then and there, but still said thank you while her voice was breaking. Inside, I felt the remorse and guilt of treating her that way, but my pride didn't let me say sorry.

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25. Brace Yourself

I had braces as a teen and then proceeded to neglect my teeth for the next 20 years. I blame my laziness and most of all I blame sugar. I had way too many Mountain Dews and too many days of "I’ll just brush my teeth tomorrow". Before I knew it, my teeth were riddled with cavities and peeling enamel. You don’t appreciate teeth not hurting until they are.

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26.  Don’t Listen To Gordon Gekko

Not pulling out of the stock market when I was crushing it. I turned $6K into $60K with a few good gambles and research. I put a majority of the earnings into a massive gamble, only, it turned into a disaster: it simply didn’t pay off. With my remaining money I tried to climb back up, but now I’m under $1K. I lost everything—all the money I had been saving over the past few years.

As a result, I no longer have the ability to move back to my home state or go off to college with my friends. I am forever in regret for missing a golden opportunity because I thought that $60,000 wasn’t enough for me and my greedy butt.

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27.  Not A Slam Dunk

When I was in high school, a kid who ran more with the popular crowd signed us up for a school-wide two versus two-basketball tournament. The idea of it was appealing, but I was scared of looking foolish.  I made sure to wear pants and shoes I could run in but then HID during the period it would be going on. I had this idea in my head that he should find me before I'd participate. I wish I'd just faced my fears and tried it out.

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28. Late Bloomer

I did all right in school but I was very shy, and looking back, I see so many missed opportunities glaring back at me. I didn’t even have my first date, boyfriend, or kiss until well after high school. My biggest regret is not telling the boy I liked how I felt, or even just speaking my mind. I only keep in contact with one person from high school, so I don’t even know what I was so afraid of.

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29. Cross Country Catastrophe

My husband and I moved from NC to Seattle in 2012. It was supposed to be so he could get a better job, which he did, with one of the tech giants. We have four kids. Not only did I develop severe seasonal affective disorder, but also my husband was suddenly working insane hours. My oldest daughter became so out of control that my husband and I had to separate so he could finish raising her. I regret the trauma I put my kids through.

After four years I told my husband I couldn’t take the rain anymore, packed up the younger kids, and left. After six months my husband followed. That was four years ago and nothing has been the same. My husband still works crazy hours for the tech giant, but from home. We don’t get to spend much time with him. Our out-of-control kid stayed in Seattle and we almost never see her.

Basically, our lives will never be the same. My 20-year-old daughter had made a nice group of friends in Seattle and was devastated when we left. Her social life never recovered. My marriage never recovered. Our old friends moved on in the time we were gone. We have no social life now, no support system. I divide up my life into before and after. That move destroyed my family.

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30. Mama's Boy

I’m always saying yes over and over again to everything my parents want. So much so, that it’s really hard for me now to stand up and say what I really want. Over the years, I have always been saying,  "Sure mom and dad, I’ll do that so you are happy," instead of doing what actually makes me happy. I'm working on it, but I wish I'd never been a "mama's boy" in the first place.

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31. Career Moves

I regret not doing a fuller investigation into what possible career options I had before going off to college.  I also regret not even making the effort needed to have taken charge and change course mid-career. Fear has held me back every time. I just retired from a career that was satisfying, but one that was probably not the best match for me.

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32. Holy Smokes!

I tried to light an old burn barrel full of cardboard once without knowing that the materials in it had been soaked in some kind of chemical that was actively vaporizing. I leaned over to drop the flaming piece of cardboard from my hand and WHAM! No eyebrows or eyelashes. It happened the day before I was supposed to attend my first day of apprenticeship schooling.

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33. High School Trip Dropout

I regret not having more fun, taking the bull by the horns, sowing my wild oats—all that good stuff. Instead, I was pretty focused on doing well in school and being prepared for university so I turned down a lot of opportunities to do some neat stuff. Our senior trip was to Japan and I dropped out at the last minute to save the money. I was still broke while in university, so I should have just gone.

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34. Time To Move

I regret being overly friendly with my neighbor because now she won't respect our boundaries. I actually found her IN my house one morning when I got out of bed and went down to my kitchen. I caught her just walking around like she owned the place. But that's not all. She's always asking us to watch her kids, without actually asking us. She is one diabolical lady.

She just literally leaves her kid home alone, and then sidles over to my place to ask if I can watch her one kid while she takes the other kid to school. However, before I can say "no," she just walks away.  I guess she just assumes I would do it? We own, she owns, there's no way of putting an end to this without making things awkward.

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35. Pushing The Boundaries

I didn’t force myself to interact in more socially uncomfortable situations, and I see now, that it was a missed opportunity. Your teen years are the freebie years you get for learning social interaction properly. There are solid odds you will never meet any of those people again, and even if you do, you can write off most anything as "WOW, we were awkward then, huh?" and laugh about it.

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36. Coupled Up

I've had long-term relationships since middle school, and it made me grow up so much faster than I needed to. I dated a boy from sixth to seventh grades. When we broke up, I only waited a few months until I started dating another guy. That relationship lasted from seventh grade until my freshman year of college. Right after that, I started dating my current boyfriend.

While I love my current boyfriend, and I wouldn't trade our relationship for anything in the world, I regret the last two relationships I had, because I feel like I threw away a lot of great years nursing foolish infatuations. I always chose to hang out with my boyfriends, instead of my friends. Everyone says that you grow the most while single, and I've never had the chance.

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37.  Never Too Young

Not going to visit my grandpa in the hospital before he passed on. I was almost seven and I wish my mother had forced me to see him. I was always so close to him, and he was like a father to me.  The last times I had seen him he was sedated. He couldn't move or speak, but he could hear us. When I saw him like that, it scared the living daylights out of me.

I just wish I was older so I could have told him how much I loved him, and just expressed more to him. I wish I had gone to see him one last time while he was still able to respond to me. I'm sure he had so much to say to me. I'm sure he was upset that he didn’t get to see me one last time. I really wish that he were still here.

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38. Rookie Mistake

When I was younger, I made a really dumb mistake as a rookie software engineer. It was a mistake that could have bankrupted the company that I was working for at the time. I spent an entire weekend trying to fix the situation. I can’t disclose what I did, but it caused me such trauma, that now whenever I make a mistake at my work, I am instantly brought back to that moment.

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39. Debt Vs. Don’t

Some say you need a Master to get a job, but I'm here to say DON'T WASTE YOUR MONEY. Very few of my co-workers have Masters Degrees and most of the jobs I have gotten over the years have been based on personal connections and demonstrated skills. I don’t think that my graduate school skill set has offset the negative effects of my student debt. I'll be paying it off for years, and I never even needed it.

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40. No Way Out

Be sure you really know who you are marrying. The family. The friends. The acquaintances. How they act when they are angry, sad, or happy. How they spend money and how they save money. Otherwise, you could end up 31 years unhappily married like me. We have a special needs daughter who needs us together in the same house, so I'm locked in, and so is she.

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41. Mum's The Word

My mother was one of those moms that yelled for everything. She wasn’t happy with my dad so she took it out on me. But weirdly enough, this made me choose friends who were just like her—loud and obnoxious. I had friends who were nice and kind, but for some odd reason I gravitated to these mean girls. And my goodness, the way they treated me was unbelievable.

Now I realize they kept me around to boost their self-esteem. I stuck around because it was something I was used to doing. I knew then something wasn’t right. Why would a friend be so negative towards me?  They were just mean. I really regret not sticking up for myself or being strong enough to choose the good people.

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42. Biting It On Bitcoin

When I was in college, I had a few thousand dollars saved up and wanted to invest some of it. I'd just read about bitcoin and thought it sounded cool, so I tried to buy some. It was brand new and you could only buy it a couple ways and had to transfer your money in certain ways. I had to set up several different accounts and wait for a deposit to be withdrawn from my bank so I could confirm the amount.

SiriusXM became a penny stock around the same time. I ended up putting my money into that instead because bitcoin was too much of a hassle. I put $3,000 into SiriusXM and sold it a few years later for around $20,000, a pretty good return. But I often think about how different my life would be if I'd just taken that next step and followed through on the bitcoin. It was $0.16 at the time. I could have been ridiculously wealthy.

Worst Mistakes FactsPixabay

43.  Father Knows Best

A big one for me is not listening to my dad's career advice. Since about eighth grade, he suggested that I look into industrial instrumentation. I thought that sounded stupid, so I went to school for aircraft maintenance. That turned out to be a field with low wages and lots of stress, so I got out. I tried my hand at IT, which I enjoyed a lot more, but again, terrible wages and a lot of stress.

Finally I thought I'd take my dad's suggestion to heart, and met up with an instrument tech to hear about his job. I signed up for school, and now I'm in a job I enjoy, making nearly double what I would have made in either aviation or IT. If I had listened to my dad prior to my six years of false starts, I'd at the very least have earned a lot more by this point in my life.

Unforgettable Comments FactsShutterstock

44. The Wrong Path

Binge drinking at 15 led me to bad friends, which led me to using other substances. I was mainly just curious. My parents were against drinking. We never had booze in the house. It was like this huge elephant in the room. They never discussed drinking with me; it was always just "never do it or you're grounded!!" It seemed like such a fun time so I wanted to try it, but it led me down a path of addiction early in life.

Biggest Regrets FactsShutterstock

45.  Serial Decliner

I'll be invited to go to conferences or collections of study sessions and agree to go. Then, when the event comes along, someone will ask me, "So, you coming to x?" I'll always respond, "Sorry, but I'm busy," when I'm probably doing nothing. They are always really interesting sessions with people I would have wanted to meet and learn from. I always regret it.

Ended Relationship factsShutterstock

46. Bookworm

Doing college right. I focused on my studies and classes. I completely ignored the social aspect and getting to know yourself parts of the college experience. I came out of college with great grades, but without any friends and no better understanding of who I am. It’s a lot harder to fix that after college. Kind of missed that train.

Biggest Regrets FactsUnsplash

47. No Regrets

Absolutely nothing. Zero regrets. Every choice I’ve made, whether good or not so good, however you define those terms, has brought me to where I’m at today. I’m alive, with three great kids, a beautiful wife and a great job. I’ve had ups and downs and even a few inside-outs, but I think living with regrets is a terrible way to go. All are experiences and I’m thankful to have lived through them. I try to learn from all of them and be happy to be alive.

Biggest Regrets FactsShutterstock

48. Proud Mama

When my parents split up, my mom had to raise us by herself and we were really poor. Eventually, we had to get on food stamps to survive. My mom was devastated. She was a very proud woman and was working two jobs, but it wasn’t enough and it absolutely crushed her to have to get assistance. It made her feel like a failure who couldn’t take care of her own kids.

I remember we were in the grocery store and getting ready to pay. She was going to use food stamps and was so ashamed that she turned to me and said, "If you don’t want to stand in line with me you don’t have to". She was trying to spare me the embarrassment. So I didn’t stand with her.  I went off and looked at a toy or something. I remember looking back at her and she was sheepishly fixing her hair.

She was trying not to look "poor" while she worked up the courage to face the cashier. I have regretted walking away so many times over the years. I was just a kid. I wish I could go back in time to go stand next to her, tell her how proud I am to be her son, and how thankful I was for the sacrifices she made just to keep food on the table for us. It honestly breaks my heart every time I think about it.

Most Cringey Slip-Ups FactsUnsplash

49. The Dreaded In-Laws

After we moved in with our in-laws in order to help them out, I realized I'd made a huge mistake. My father-in-law’s nonsense has literally put my gay son off from eating with the family. None of us are perfect, but their ideas are completely twisted. For some reason, they keeping arguing that they're the ones helping us out. The fights that have ensued are absolutely ridiculous.

Not to mention the've caused a £500-£700 decrease in my income because they don’t give me any space for my clients to visit.  We had agreed on one room so that I could work, and this was even before COVID. But that's not all. They’re the pickiest eaters I've ever met,  and even though it is health-based, it’s expensive. Basically, my in-laws are toxic. And I regret moving in with them in the first place.

Biggest Regrets FactsShutterstock

50. Out In The Cold

When I was 10 and my sister was seven, I wanted to go play in the snow and none of my friends were out so I invited her to play with me. She was super excited but it was going to take her a while to get her snow clothes on and I was already dressed so I said I’d wait for her out front. While I was waiting, a friend came by and invited me to play. What I did next was absolutely despicable.

Without even thinking twice about my little sister, I abandoned her and left with my friend. I came home an hour or two later to find out that she went outside looking for me for a while and came in broken-hearted because I wasn’t there. I’m in my late 40s now and while she’s never once brought this up, I think about it often and cringe.  What a terrible thing to do. I can't imagine ever forgiving myself for it.

Biggest Regrets FactsLibreShot

Sources:  Reddit,

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