Regretful People Share “I Knew I Shouldn’t Have Done That!” Moments

November 5, 2023 | Miles Brucker

Regretful People Share “I Knew I Shouldn’t Have Done That!” Moments

We all do stupid things from time to time. People make honest mistakes, and that’s to be expected. What’s less expected is when we approach something, realize it would be stupid to actually do, and then proceed to do it anyway.

In those moments, it’s hard to have any reaction besides instant regret, a solid palm to the forehead, or head to the desk, followed by an exclamation of “I knew I shouldn’t have done that!”

Here are 42 examples of actions that might make people think twice the next time they feel like doing something stupid.

1. That’s Why Pencils Have Erasers

When I was six years old, I once stuck my little finger into a pencil sharpener and twisted it around a few times like it was a pencil.

I nearly passed out.

Shouldn’t Have Done That Facts

2. There’s No Place Like Home

I bought the house we had been renting for a few years without getting a proper inspection first.  We were trying to do it for super-cheap, and I told my wife, "Look, we already know everything that's wrong with this house. Why bother getting an inspection?"

Follow up: We did not know everything that was wrong with this house--nor did we realize how expensive it would be to fix those things.

Shouldn’t Have Done That FactsMax Pixel

3. Putting This Incident Behind Us

In seventh grade, I once accepted a dare to smack a girl on the butt.

It turned out the principal was standing 10 feet behind me and saw the whole thing. He took me straight into his office.

Shouldn’t Have Done That FactsShutterstock

4. Iron Man

I was once ironing my clothes, when I decided to try putting the iron on the carpet while my mom was out shopping. That went well.

Shouldn’t Have Done That FactsPixabay

5. Never Pulling a Stunt Like That Again

When I worked as a stunt performer, my last performance was with a particular stunt group. They wanted me to do a particularly dangerous version of a stunt that I already didn't love, so I felt pretty uncomfortable. I had done the regular version thousands of times and could practically do it in my sleep, but this new version worried me.

I agreed to do it because it was just gonna be the one time. What were the odds of getting hurt doing it just the one time, I thought!

Later that day, I found myself in a second hospital after being airlifted from the first one because my injuries were too severe for them to handle. I had literally a gallons worth of blood transfusions (they weighed me before and after), and a life-saving surgery.

If you have a bad feeling about something, take it seriously.

Coma Survivors FactsShutterstock

6. Let’s Face the Music

I once bought Metallica's newest album on CD a while back. When I got home, I remembered that I didn’t have a CD player…

Shouldn’t Have Done That FactsShutterstock

7. Grabbing the Idiot by the Horns

An aggressive idiot started walking away from me one time, and my amazing brain came up with "Yeah, you better walk away!"

He then turned around and I nearly pooped my pants.

Paranormal FactsShutterstock

8. Horsing Around

I'm five years old and my next door neighbors take me to meet their horses. The mom gives very clear and explicit instructions on how to handle the horses properly, and proceeds to start brushing one of them. In my infinite wisdom, I defy all of the instructions I just received and walk directly behind the horse to very timidly graze its beautiful tail with my small hand.

With lightning speed, I'm hit with a degree of force that I wouldn't again feel until I was in a huge car accident many years later as an adult. I'm launched out of the stall and fly halfway across the common area until I thump down on the floor. As I lay there, stunned and gasping, for breath, I know that I definitely should not have done that.

Shouldn’t Have Done That FactsPixabay

9. You’re Toast!

I touched the coil in a toaster with a blade while it was switched on.

When the power in the house cut out, I realized I probably should not have done that. When I told my father what I'd done, I knew for sure that I should not have done that.

Funniest Comments Anesthesia Patients Made factsShutterstock

10. Speed Eater

I once ate three packs of noodles and 12 meatballs in under 20 minutes.

Bad idea…

Shouldn’t Have Done That FactsShutterstock

11. Operation Uh-Oh!

I enlisted in the army, completely on a whim. By day two, I knew that I had made a big mistake…

Close-Up Of Soldiers In A RowGetty Images

12. Thanks, But No Thanks

When my girlfriend broke up with me, I was completely caught off guard. As a result, I stupidly blurted out "Okay, thank you".

I shouldn’t have done that. It has made many things very awkward ever since.

Shouldn’t Have Done That FactsShutterstock

13. Jumping For Joy

During fourth grade, my parents remodelled our kitchen. This involved digging up part of the foundation to rebuild the deck. As such, we had a giant pile of dirt in the backyard.

When I went to play on it (who can resist a pile of dirt, am I right?), I jumped off, tripped, and fell face first not into the dirt but onto the concrete beside it. Immediately, I knew that something was wrong. I ran inside, opened my mouth, and looked in the bathroom mirror to find that I'm missing about a third of my top right front tooth.

I distinctly recall saying out loud, "Yup, it's gone" and regretting having attempted the jump.

Shouldn’t Have Done That FactsFlickr

14. Fancy Pants

I spent about $200 on new a new pair of pants, only to find out I was pregnant the very next day.

Shouldn’t Have Done That FactsFlickr

15. Five’s a Crowd

I once ordered five Arby's roast beef sandwiches for $5.

The regret started sinking in around the time I got to sandwich three.

Shouldn’t Have Done That FactsWikimedia Commons, Lenin and McCarthy

16. Wok and Roll

I got distracted while my wok was heating up with some oil in it. When I snapped back to reality, my hand just automatically threw in the dried chili flakes. It was like an out of body experience. My brain couldn't stop my hand in time.

And that's how I maced myself...and my dog.

Shouldn’t Have Done That FactsFlickr

17. A Royal Flush

When I was a kid, I was horsing around and ended up totally destroying one of the house plants by accident. No kid wants to get in trouble so I decide to get rid of the evidence. How? Flush it down the toilet, of course!.

So I walk into the bathroom feeling like I got this but none of the dirt goes down at all, obviously. I'm panicking, just flushing and flushing for 20 minutes straight. It all goes down eventually but I probably destroyed our plumbing system. Whoops...

Shouldn’t Have Done That FactsShutterstock

18. Getting the Message

My no-good ex sent me a "Hey, how've you been?" message on Facebook. I stupidly responded.

Internet factsFlickr

19. Um...What??

I gave a speech in high school arguing that the way to solve the issue of single parent families was simple. Obviously, the government should just subsidize restaurant dinner dates so that poor women could get asked out more often and see men interact with waiters in order to reveal their character, thus enticing them to marry nicer men.

By the looks on people’s faces in the audience while I was speaking, I quickly realized that what I was saying made little sense.

Cringeworthy Dates factsPxHere

20. First Time’s the Charm

I got married at 19 to the first girl I ever slept with. We had nothing in common.

I probably shouldn’t have done that.

Shouldn’t Have Done That FactsMax Pixel

21. Won’t Be Needing This...

When I was six years old, I hung out with a few neighbors around the same age in the back area of a local park, where we found this weird shoebox, half-buried near the edge of a creek. We were apprehensive at first, but in the end we dug it up and opened it, finding a few ziplock bags of white powder, which I immediately thought to be some kind of drug. We ended up just tossing the bag into the water and leaving it there.

In hindsight, throwing away what might have been a convict's expensive drug was probably not smart. You generally don’t want to get on those people’s bad side…

Childhood Lies factsShutterstock

22. An Offside Throw

Our toilet is opposite the laundry hamper in my bathroom. I undressed for a shower one day and casually tossed aside my socks...into the toilet. As soon as they left my hands, I let out a strangled "Nooooo!!" which sent my husband running in, presumably to help me, though once he saw what happened, he just laughed at me for the rest of the night.

Nicest Compliment FactsShutterstock

23. On the Road Again

My sister offered me her old car for free. She said it was really reliable, so I took her word for it and didn’t do any inspections. I flew down to New Orleans to get it and decided to take the scenic route back home.

Where am I writing this, you ask? I am currently sitting on the side of the road in one of America’s largest swamps with what I suspect is a busted timing belt. Just waiting on some redneck vampires to show up at this point…

Shouldn’t Have Done That FactsShutterstock

24. Hello, Dolly

I once lost control of a dolly and the refrigerator that was strapped onto it. When it started bouncing down the stairway like a rocket, I had the thought that I probably shouldn’t have been so careless with how I handled it.

My suspicions were confirmed a mere second later when it slammed full speed into the concrete wall at the bottom of the stairs and came to a stop. Not surprisingly, the refrigerator never worked properly after that, so I immediately had to lug it back out of the basement and best of all, pay for the damages. 0/10. Would not recommend.

Self-Diagnosing Patients FactsShutterstock

25. Home Alone

I decided to go to my insane ex's house alone to pick up my stuff that I didn't actually care about.

We had broken up recently because she tried to stab me when I got home from drinking at the bar with a few friends.

Thankfully, I lived to tell the tale.

But I still probably shouldn’t have done it.

Shouldn’t Have Done That FactsShutterstock

26. Cookie Monster

I once microwaved raw cookie dough. That did not end well…

Shouldn’t Have Done That FactsFlickr, Marco Verch

27. You Probably Should Have Kept That Private...

When I was around 12 years old, I noticed that nail polish remover felt cold and kind of nice as it evaporated from my fingers.

So I decided to put some of it on my private stuff…

Shouldn’t Have Done That FactsShutterstock

28. The Wayward Wind

I sailed my boat on the lake one afternoon when I saw a strong gust of wind incoming. Nevertheless, I didn’t feel like docking and thought I could handle it, so decided to push my luck.

Needless to say, we capsized.

Shouldn’t Have Done That FactsPixabay

29. Chances Are

After many years of refusing to see him, I finally gave my abusive dad a second chance to be in my life. He hadn’t changed at all.

People Who Struggle With Mental Health Share the Moments That Finally Made Them Seek HelpShutterstock

30. Nothing Festive About This Experience

I was at a music festival and decided to use the outdoor public bathroom.

Bad idea...

Shouldn’t Have Done That FactsPexels

31. You Can’t Make This Stuff Up!

I was once at a local shopping center looking for a job, feeling pretty lousy, and pretty darn broke. This salesman approaches me and somehow, I get talked into buying a massive makeup set. I don't even wear makeup!

Shouldn’t Have Done That FactsPixabay

32. A Lesson He’ll Never Forget

In my first year teaching, a boy in my class made fun of my receding hairline.

It was only the second week of the school year and I still wasn't used to how I was supposed to behave as an educator, so I just blurted out "Oh, f*** you!"


Bettie Page FactsShutterstock

33. Unholy Matrimony

I got intimate with a married coworker.

It happened a long time ago and I was in a really bad place at the time. I realized right away that I shouldn’t have done it, and I still feel guilty about it.

Shouldn’t Have Done That FactsShutterstock

34. A No-Win Situation

As someone who is lactose intolerant, any time I decide to consume a dairy product I instantly get the “I should not have done that” feeling.

And no, the pills do not stop the impending doom that is butt lava.

But what am I gonna do, quit pizza? Never!!

Buffet Workers Horror Stories FactsGetty Images

35. Identify Yourself!

I met a guy online through a language exchange program. We ended up talking about this and that, and the subject of ugly ID pictures somehow came up. I wanted to show him my funny ID pic.

Yes, ladies and gents, that is how I accidentally leaked my full home address to some sketchy stranger on the internet.

Online Friends FactsShutterstock

36. Instant Karma

I once pushed a pot of hot oil off of my friend’s stove top as a joke.

The funny thing about physics, though, is that the oil splashed right back at me and landed all over my hand.

Shouldn’t Have Done That FactsPixabay

37. Dishing It Out

I had some dirty dishes from spaghetti and I was out of the detergent that's made specifically for the washer. Obviously, I don't want to wash them by hand so I just pour regular dish soap into the machine, feeling like MacGyver.

I didn’t realize how wrong I was until my entire kitchen looked like a foam party. Definitely should not have done that.

Shouldn’t Have Done That FactsFlickr, Your Best Digs

38. Too Much Information

While interviewing for a really great job offer at a government department right out of college, I casually mentioned the fact that I smoke weed regularly.

The government did not like that and my offer was quickly revoked.

I probably should not have made that comment…

Still Mad About FactsShutterstock

39. Food For Thought

I have the “I shouldn’t have done that” feeling each and every time that I buy drug for myself instead of food—which happens more often than I’d like to admit…

Sad Man in plaid blue shirt sitting outside in front of a lakeNathan Cowley, Pexels

40. You’ve Got a Friend in Me

I once told a girl who liked me that she was my best friend.

Looking back, it was possibly the stupidest thing I have ever done.

Shouldn’t Have Done That FactsShutterstock

41. Hold Your Tongue

I told a friend with a speech impediment to stop stuttering.

Marion Davies FactsShutterstock

42. The Glass Is Always Half Full

I broiled burger patties on a shallow cookie sheet, causing the small lake of grease that accumulated to catch fire and nearly burn down the house.

On the bright side, the burgers were great!

Shouldn’t Have Done That FactsFlickr

Sources:  Reddit, ,

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