While regret doesn’t always feel good, there are some positive aspects to it, believe it or not! Regret often teaches us things about ourselves and what we want in life. It helps us think more carefully about decisions in the future and not make the same mistakes again. Even hearing about other people’s regret can be useful and enlightening. On that note, here are ten stories where people share their biggest regret in life. This content has been edited for clarity.
“I was never very emotionally mature. From a very young age, I locked up any deep emotions and buried them so deep they had a very hard time ever surfacing. That said, I was a very happy-go-lucky guy growing up. I made friends easily although I was never really good at deep relationships. When I met my wife-to-be through a friend, I knew she was the one for me, just from her personality. Thing is, I was never good at meeting her needs. Hell, I didn’t know or understand my own needs.
Basically, I was a bad husband and was too oblivious to realize it. I was embarrassed by communicating, I was embarrassed by sex, I wasn’t confident, and I always had a secret addiction to porn. The one thing I had going for me was the happy-go-lucky thing, it never let me down. Fast forward 10 years into our marriage, my happy-go-lucky just up and flew away one day. I never knew where it went– I guess I was just ready to change and grow up, though I refused.
Fast forward again about 20 years into our marriage. She has suffered from depression most of her life and had just taken herself off of Zoloft which had made her a zombie for years. She was trying to focus more on us since we’d grown apart. Meanwhile, I was at my wit’s end, didn’t know how to keep coping, had thoughts of suicide, and still didn’t turn to the one person who wanted to be there for me. I struggled on my own until I met a girl at work I could relate to and finally started opening up. I was like a teenager at that point, pathetic!
I invited so much drama into my life, it was sick. The relationship with the other girl built up to one sexual encounter at which point I finally grew up. It’s like my eyes were opened and I finally saw myself in the mirror for the first time in my life. It was shocking and horrible. The hardest thing I’ve ever had to do in my life was telling my wife I had an affair.
At a time when my wife who loved me and never left me was at her most vulnerable, I kicked her in the teeth. I will never forgive myself for that, I just won’t. I’ll never deserve that. We’re still together and I’ve grown up, although I took way too long to do it. I take good care of us as a couple and my family, but I will never be able to look back at my former self without shaking my head with regret for who I was.”
Too Little Too Late
“I had been best friends with this girl until a year or two later when I decided to ask her out. From that point on, we dated for five years. I neglected so many things in our relationship. Even though in my heart I knew I loved her more than anything, I couldn’t ever put my pride aside and be the person I needed to be. She has the biggest heart of anyone I have ever known in my life in that she stuck through five years with me not giving her what she deserved.
I was unambitious, unmotivated, and self-loathing, but I would’ve never admitted any of that while I was with her. She still loved me because we were best friends. We had done everything together and never spent more than a few days apart. For the last two years of our relationship, she had been very adamant about marriage. She had even taken me into a shop that was selling an antique ring she absolutely fell in love with. Every time we’d walk past the shop, she would ask me if we could go in and see if it was still there.
On new years eve I had planned to ask her hand in marriage. I invited friends, her family, my family, and we had a ‘new years’ party. Unbeknownst to her, we weren’t all there for new years, but rather the ensuing engagement. She spent all night saying, ‘It’s almost our anniversary!’ I kept playing it off cool saying, ‘I know babe, I can’t wait to go out tomorrow!’ I tried not to hint at anything big. At midnight we kissed and celebrated with everyone while drinking champagne. At about 12:15 am everyone slowly started gathering in the living room. My girlfriend was sitting on the fireplace ledge (which was perfect for me to kneel down to her level) and everyone else was sitting around.
I cleared my throat and began, ‘Excuse me, everyone, can I have your attention please?’ I had the biggest smile on my face. ‘It is now 12:20 am on January first, 2014. This is exactly five years to the day and to the minute we began dating. Now, five years later (I turned around to face her and knelt down in front of her with the ring), I would like to ask you to be my wife.’ She burst into tears of happiness and embraced me and we kissed while everyone else cheered. We celebrated the rest of the night until we could barely stand. Every time she would look at her new ring, she would smile so big with such happiness.
One week later, on the eighth of January, she left. She said she did not feel happy and that she had finally reached the point of carrying too much weight on her shoulders. All those years she was so strong. She put up with me neglecting not just her, but myself. She was always so encouraging and accommodating. I just wasn’t able to give her the support and sacrifice she needed me to, both financially and emotionally and that is my biggest regret in life. She insisted it was something she should have done a long time ago and apologized for never speaking up before. She insisted she needed time to herself to find who she was as she had never given that to herself, and I never was able to allow it to happen.
That girl means the world to me. I truly believe she is my soul mate, my best friend, and a once-in-a-lifetime love. I am doing all that I can to take care of myself in a better way now in hopes that she will see that it’ll be worth it. I cannot walk away from five years of loving this girl and the thought of marriage and a future with her for eternity. I will never give up on her. I will never stop doing what I need to do; what I didn’t do. I love her with all of my heart.”
“At age 16, I was sent to a ‘therapeutic boarding school’ called The Elan School which ended up being nothing more than a psychologically torturous cult. I remember on my first day sitting in a ‘dealing crew’ and they were telling me that I would be lucky to leave in three years. My obvious first instincts were to plan an escape. As weeks passed into months, my resolve to escape only got stronger as I watched some of the most bizarre and psychologically damaging rituals I have ever seen in my life. I couldn’t even believe my own eyes, but there I was, watching it happen, seeing the ever-growing net around me, struggling to make me one of them.
I was planning my escape which required getting past the guards who were other residents of the house. I realized it would be hard to run at night because every 15 minutes someone was counting us while we slept. During the day, the headcounts were every 10 minutes. As I worked out the details of my plan, I realized two would be better than one. I needed an accomplice. But because I was deemed a ‘new-resident’ and a ‘non-strength’ in the program, it was against the rules for me to talk to other non-strengths. However, I simply could not trust anyone who had been in Elan long enough to be brainwashed, so I had to find a way to talk to another non-strength.
There were people everywhere with clipboards taking notes and literally watching your every eye movement. Part of ‘the program’ was ‘holding people accountable’ which is Elan-speak for ‘rat everyone out and you will get more privileges.’ I was able to start making quick eye contact with another new resident, we will just call him Jim. After a few weeks, he seemed to get my signals and he had not yet ratted me out. He knew full well we were ‘acquiring guilt’ by looking at one another and sometimes adding imperceptible nods.
And then something really messed up happened. A third new resident had started to do to me what I had been doing with Jim. I was not yet at the point where I would rat him out for it, but I began to notice the way he would throw me very subtle signals. There was no possible way he knew about me and Jim. It was like he was trying to form his own bond with me. Let’s call him Martin.
Martin was pressured by someone in a higher position who had decided he had seen ‘guilt’ in his face. As a result, Martin ratted me out. Then Jim got pulled into it too because this Martin had also been throwing him signals. Long story short, we all got put on a ‘bright LE’ meaning we had to wear bright clothes: a yellow t-shirt and pink girl’s shorts. And on top of that, we were put on 10-foot bans from one another meaning that none of us could be within 10 feet of the other.
That made all of our lives extremely difficult and running away with Jim became basically impossible. I had figured the next step would be to slip him a note while we passed in the hallway, but now that was impossible. We had a house trip planned in a few months to a place called Fort Williams in Maine. All of the residents who ‘earned it’ would be allowed to spend one day outside of the complex. Of course, there would be guards there too, but my mindset was that it was already closer to a possible escape. Where the complex was, it would take six or seven hours just to reach civilization. If I ran at the Fort, the possibilities could be endless.
But I didn’t run at the Fort. The Elan program had already begun to take a hold of my mind by that point, about five months in. I still had a sliver of hope though. There was a trip to Boston once a year, once again for the people who ‘earned it.’ Maybe I was just making excuses by that point, but I began to tell myself that Massachusetts was multiple states closer to my home. It would be far better to wait another few months and then make my escape from there.
But I didn’t. I continued to underestimate the psychological hold living in a cult can have on a person once given time. And this is how my life was for the next two and half years. Always putting off my escape for the next ‘best’ time. But every day longer that I stayed in the program, my mind became a little more Elan-ified. After about 15 months, I was actually stopping other people from running away.
My biggest regret is not trying to escape. Sometimes I dream about going back in time and running away from that place. I turned out okay anyway, much better than most of the poor souls who ended up being stuck there for years on end. But I will never, until the day I die, stop wondering about who I would be today if I had bolted.”
“I’m 23 and have been with my boyfriend since high school. I don’t regret our relationship or that I’ve stayed with him for so long, but since he was my first love, I regret that I’ve risked almost everything for him. I’ve risked my parents’ trust, risked my credit by taking out loans for him, and risked the money I lent him which he has yet to pay back. I gave up normal high school and college experiences because he was insecure and jealous of everything, and have given up on having a semi-normal relationship because of the way he is.
There were so many warning signs early in our relationship that he was irrationally jealous and ridiculously paranoid, but I didn’t see them because I was so head over heels in love. When he hit financial troubles due to a gambling problem, I should’ve ended it then and there because I absolutely hate gamblers. Another time I should’ve ended it was when he used pictures and videos I sent him to blackmail me into staying with him and listening to whatever he told me to do. Since I was scared of what family and friends would think if they found out, I begrudgingly stayed with him.
The blackmail was years ago and he hasn’t tried anything since because he lost the USB containing the pictures and video, but he’s only recently getting over the gambling and financial issues. Actually, he still has financial issues because I recently took out over 24K in personal loans to help him out which he promised to make the monthly payments on. I always ask if he’s gonna put money in my account to pay the bills and he actually threatened not to put it in if I kept asking. What a wonderful guy I snagged right? I’m trying my best to get out of the relationship so wish me luck.”
Should Have Ran
“My ex-wife and I met in college and began to be exclusive almost immediately. We took things slow and after graduation, I moved home and she continued at school as she was a year behind me. I was not physically attracted to her, but I fell in love with her kind and gentle personality. I moved back up to the school to be with her. At that point, I had enough information to run but thought ‘she was different.’ Her dad stopped talking to her or communicating in any form after he decided he didn’t want her dating me.
After about a year and a half, I moved to Hollywood to pursue a film career and she followed me. I was working in the film industry and she got a job doing database stuff for FOX. I had resigned myself to being with her for the rest of my life but I didn’t want to get married. She was my life partner, not my wife. My mom told me I had to marry her or I should let her go find somebody that would. I gave in to the pressure and we got married. I helped support her through her master’s degree and after a few years of what was our ‘normal,’ she got a job in a city that had an hour commute from our apartment in North Hollywood.
We eventually bought a house by her job because she made much more money than I did and she didn’t want to drive that much anymore. She forced me to get a master’s degree and became very weird. She had visited some of her mother’s family when her grandmother was dying, and when she came back, she was different. The insanity of her mom’s family was creeping in. She was getting really bad and started maxing out credit cards on things like lunch for all her coworkers.
One day, she came home and said she wanted a divorce. I tried to fix things for three months, but one day I left and she never let me back. Our eight-and-a-half-year relationship was over. I had given up my film career, given up on being physically attracted to her, given up on living in a place I liked, and given up on so many things important to me. My biggest regret in life was entering into a relationship with her. She was a virus that destroyed me and consumed my will to live. I regret everything about her.”
The New Kid
“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. 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. I was tired of being alone and wanted to conform to what I saw other kids doing, at least in appearance. I knew that people do judge a book by its cover. 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 of myself. I could tell he understood even though he thought the world of his son. He did it for me somehow though we had no money. Short hair, contacts, two pairs of jeans from Ross, and a couple of shirts. I was a completely different person. Everyone agreed I looked much better.
A kid in my class asked me to hang out and that is when I met all of his friends. I became part of their group and they accepted me readily. For the first time, people my age actually wanted me around and sought me out aside from my two real friends who were pretty much outcasts just like me. I couldn’t believe it. And that is when I met her. She was so kind and sweet and pure. She was so beautiful with golden blond hair and deep blue eyes. I never knew people could be so pretty and nice. I can still remember how she made me feel even through her friendship and I soon fell for her deeply and completely. It wasn’t mutual though and it was torturous.
She was dating another friend in our group and I was able to leave it alone in spite of craving her. Her relationship with the other friend didn’t last long and soon we were talking to each other at night on the phone until we fell asleep. I loved her so much and I told her how I felt, but she didn’t feel the same way. She was sorry but wanted to stay friends. Eventually, my love found another girl to pine over, and another and another.
School let out for the summer and I knew our group would spend a lot of time together during those carefree summer days. I was surprised when she called me up one night and asked to come over and watch a movie. During the first few minutes, she was being really strange and I was so oblivious to it all. After the movie she wanted to listen to music in my room which also struck me as odd, but I said whatever. We walked into my room and the next thing I knew, she closed the door and is all over me. Kissing me deeply in a way that had never happened before. I don’t think my heart beat for a full minute and when it finally did, I could hear it in my ears. We started dating that night and saw each other every day afterward.
Meanwhile, my father had lost his job about six months earlier and had a hell of a time finding work. He finally found a job, but we had to move to Montana. So the unexpected, unbelievable relationship that had just begun would be over just as quick and I would be away for a very big period of what was left. It was devastating beyond belief. She really was the first person I could even call a girlfriend. We kept up our relationship until the move came. I spent my last night with my two closest friends that lived an hour away and saw her one last time.
I left for Montana with tears in my eyes and the type of promises that only a 16-year-old would think they could actually keep. I had promised to write and call when I could. I told her we would go to the same college. We would keep in touch. We would stay in love. I had told her already I loved her many times. When I arrived in Montana, I became so depressed I could barely move. My days dragged on and my nights were even longer. I didn’t run a single step before Cross Country season in the fall. I had no energy and I couldn’t bring myself to write or call her, not a single time.
I regret that to this very day. I regret that I didn’t let myself feel the pain of being apart. I traded that for the pain of being alone. I understand that even if I had written and called, it would have soon fizzled out on its own, but that changes nothing. In fact, that makes it even worse. I regret knowing that for weeks she was waiting for the phone to ring and checking the mailbox every day. God, I regret that now. More than any of the other horrible things I have done to other people in my life.”
“My biggest regret is leaving a girl who loved me because everyone was telling me not to waste her time. I sat and thought about it for two months and finally decided to pull the plug. As a rare exception, we decided to stay friends. Months later, I realized we hadn’t spoken so I invited her out for drinks. We started getting close again and I realized I never saw how much she truly cared for me and I fell in love. But right around that same time, she got distant. One day, after numerous attempts to meet/talk for about two weeks, I confronted her. She told me she had started seeing someone else.
I still see her every now and then, but it’s different. There’s a lot of resentment from her end and she told me she hated me once. There was one strange night when she wanted me to hold her until the bus came at three in the morning. Besides that, it’s been a spiral of terrible ‘relationships’ and alcoholism for a solid six months. I don’t know why I still talk to her. Probably because I care enough for her to be my friend.
Moral of the story: don’t listen to your friends/family about certain things. You know way more about a situation than they do and you have to trust yourself. And if you’re in a relationship, have hard talks with your significant other. Special people you connect with are really, really hard to come by, so don’t squander that.
Oh! And one more thing. Those little perfect moments? Enjoy those. I barely remember mine, but I do remember a few. That perfect morning when you’re going to be late for work if you don’t get out of bed? Stay in bed. Show up 15 minutes late. But absorb that moment like a sponge, because that’s the big secret to life– perfect moments. Nothing more.”
One Last Time
“My father started struggling with idiopathic pulmonary fibrosis as his lungs were turning to scar tissue and no one knew why. We had been working with Duke Medical Center to explore the possibility of a lung transplant. He had just returned home from a multi-day battery of tests and examinations and was feeling pretty good about his chances when he fell ill with what appeared to be pneumonia and was hospitalized. He was having even more difficulty breathing 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) 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 a temporary drug-induced coma. He was fighting the ventilator and in a lot of pain, so 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.
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, but it would have been my last chance to speak to him. I also felt 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.”
“When my dying father told me he loved me, as a sort of ‘getting his affairs in order gesture, my reaction was anger. I didn’t yell at him, I let him say his peace, and accepted it with some grace. But I didn’t say it back, even though I did and do love him. It just felt too unfair that after a tough relationship in which he made a lot of mistakes, he would get this free pass from me at the end.
Over time, I’ve come to realize that was wrong of me. In the moment, I was focused only on the negative stuff. But in reality, there was way more positive stuff. He was a good man. Over the years, I’ve let go of most of the anger and remembered more of the good stuff. Having kids of my own has helped a lot. I realize I’ve forgiven him. That being the case, I just wish I could have faked it in that moment so he could have known what ultimately was the central truth: I loved him too. I like to think he knew even then, that he was mature enough to understand my anger, and that I’d ultimately put it aside. But it would be nice to be sure.”