12 People Share Their Most Devastating Regret Ever

Mistakes and miscalculations in life are bound to happen. The most challenging part is dealing with the regret that follows. Yet, it’s crucial to remember that everything occurs for a reason.

We should view these setbacks as opportunities to motivate ourselves for improvement. In this article, people share their significant regrets, transforming them into valuable stories from which we can learn.

• 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, 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.
  Once, I remember we were getting ready to pay at the grocery store. She was going to use food stamps to pay, and she 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; she was sheepishly fixing her hair and trying not to look “poor” as 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, but I wish I could go back in time to stand next to her and tell her how proud I am to be her son. © moby323 / Reddit

• When I was at my 10th birthday party, we were heading to a fast-food restaurant, and my mom couldn’t find her purse in the dark car. I was really hungry, and we couldn’t locate the purse anywhere.
  I remembered my friend telling me a while ago that he kept money in the back of his phone case for emergencies. I then suggested that we use my friend’s money for my birthday party to cover the expenses. Fortunately, we eventually found my mom’s purse, but it’s been 5 years, and I still feel regretful whenever I recall that incident. © penguin426210 / Reddit

• My biggest regret in life is telling my son’s father that I was pregnant. He broke up with me three days after I told him. I regret not keeping it a secret and never talking to him again.
  It’s been extremely challenging for my son ever since. In four more years, he will be an adult and won’t have to deal with his father ever again. We plan on moving to Europe. © SpiralBreeze / Reddit

• When I was maybe 11 years old, my mom took us to a clothing store. I was bored, playing under the racks, just being a mischievous kid. I noticed some 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 didn’t say a word and left with my mom.
  I was such a terrible kid. I still feel bad about it. © Unknown user / Reddit

• 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, and he walked out of the dollar store with a single can of soup.
  I should have handed him more. He bought one meal, and I spent my money on junk. It bothers me still 10 years later. © Darogaserik / Reddit

• I regret telling my mom I was embarrassed of her. I was just a typical teenager going through a stage of not wanting to be seen with my parents, but she took it personally, and I saw a flash of real hurt on her face.
  It breaks my heart thinking about it nearly 20 years later. © Mycelium83 / Reddit

• When I graduated high school, my plan was to move out of state immediately. I had been accepted to an out-of-state college that I loved and intended to attend. However, I got a girlfriend in my hometown, and I decided to stay around for her.
  We broke up six years later, and now I’m still in the state I grew up in. While I am happy and have an amazing girlfriend, a great job, friends, etc., I will always wonder what would have been had I moved to a big city and followed my dreams. © cheeseCloud / Reddit

• When I was a kid, my dad and I made a tooth costume out of an old hamper and some papier-mâché for Halloween. The day came to wear it to school, and before I even knew what anxiety was, I couldn’t bear to wear it. I cried and begged. Looking back on it now, especially since he passed, it must have broken his heart. © mcgruber55 / Reddit

• When I was friends with a girl, I started messaging her a lot after school. However, for some reason, I let a friend convince me not to talk to her because he didn’t like her.
  I had no interest in a relationship with her; I just enjoyed talking to her. But I saw the messages we sent the other day, and it was uncomfortable to look at how I turned on her. I just blew off her messages with one-word replies or straight up ignored her, even when she said she needed a friend that day. I even regret reading it because I’d forgotten how spiteful I was. © craygroupious / Reddit

• I regret not attending my best friend’s father’s funeral. Being an introvert, I didn’t want to confront her in this situation. At the time, I was going through a difficult childhood, and it made me think my problems were bigger than anyone else’s. Years later, she told me she was waiting for me so that she could hug me and cry. It breaks my heart. © anjul26 / Reddit

• I was 13 at a theme park with my class. It was our last day of school, so we went to a big park to ride some rides. Thinking I was funny, I kept telling kids in my class, “Don’t die” as they would climb onto a roller coaster. Some kids looked scared, some laughed.
  Then a 20-year-old guy with his girlfriend, also in line, turned to me and shouted, “Kid, shut up.” His girlfriend quickly tried to calm him down and said, “He’s just a kid.”
  For me, it was like I had been slapped out of a trance. I thought, “I’m annoying?!” It was the best thing to ever happen to me, I think. But I do cringe when I think about it. © D***LO258 / Reddit

• When I was 10, and my sister was 7, 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 waiting, a friend came by and invited me to play, and I went without even thinking twice about my little sister.
  I came home an hour or two later to find out that she went outside and looked 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 and get pretty down about it. What a terrible thing to do. I cannot imagine ever forgiving myself for it. © buckeyecarlweb / Reddit

Job interviews can sometimes leave us with a strong sense of regret afterward. It could be due to something we said that jeopardized our chances of being accepted, or it might be the decision to attend the interview in the first place. The narratives in this article revolve around job interviews that turned into pure nightmares. We’re curious to know if you’ve had a similar experience.