“Why God?!” Cringing Adults Confess Their Most Embarrassing Childhood Memories

Ah, childhood. The time we always look fondly upon and wish we could go back to. Well, maybe not all of us. In fact, for many of us, our main childhood memories are memorable for all the wrong reasons. From epic fails to the ridiculous actions that our not-yet-developed brains made us think were good ideas, the list of embarrassing childhood memories goes on. Here are the childhood stories people wish they could forget.

1. There Will Be Blood

I was seven years old and my parents were hosting a family and friends gathering at our home. During these types of events, I mostly stayed out of the way and played video games in the living room. The adults would frequently walk by and ask me what I was playing and whatever. It was always nice. A few hours into this particular party, I decided that I wanted some soda. This is where it all went wrong.

I go to the fridge and see one of those little ice breaking hammers, and I proceed to stick my tongue onto it like the cartoon characters always did, just to have a little laugh. I pulled it off immediately and there was blood everywhere. I ran into the other room crying, with my bloody tongue sticking out, to the absolute horror of every single adult who was over.

Now, you’d think this would be the big moment, but it got so much worse. A family friend who was a doctor was there and he came over to me, saw my tongue, and told me: “I think it’s fine, I just need you to spit out some blood so I can get a better look.” I proceeded to spit my entire mouthful of blood directly into his face. Every single person that saw it lost their mind laughing. Even the doctor himself!


2. I Walk The Line

My most embarrassing childhood memory is of the time when I pooped on the floor between arcade games at the age of seven. But it’s why I did it that’s the most mortifying. I did so knowingly, because I didn’t want to lose my place in line to play “Gauntlet.” I guess I didn’t think that anyone would notice what I was up to. I was wrong. People did notice. And I lost my place in line, permanently…


3. Spreading The Love

One time, I was in a shopping mall when I heard someone say my name. At least, it sounded like my name. I looked up from my phone to see this pretty girl walking towards me with outstretched arms and a smile. She looked so familiar, like someone I knew from my high school. So, of course, my dumb, nearsighted self, opened his arms wide to receive and reciprocate the hug. It hurts to remember what happened next.

She side-stepped around me neatly like a ballerina-ninja and delivered the hug to its rightfully intended owner, who was right behind me in my blind spot. Evidently, this gentleman must have had a name that sounded something like mine. Her side-step left me fumbling to play off the most embarrassing moment of my life. I still cringe when I think about this.

After hightailing it out of there, with my dignity in shreds, I met up with a few friends and I was able to put the entire debacle behind me. Only it wasn’t over. I ran into ballerina-ninja and the hug thief once again, who by a supreme “screw you” by the universe had been joined by a couple of their friends. I glanced in their direction, and saw her nudge her friends and whisper something while pointing in my direction. Then they all laughed.


4. Off To The Races

My most embarrassing childhood memory is of the time I put a piece of toilet paper in my butt like a horse tail, and started running around the house naked with cups on my hands and feet as hooves. I’m sure there is a picture of it somewhere, but I have no idea where or who would have access to it. If social media had been around back then, I would have been roasted.


5. Poor Word Choice

Oh my gosh, most embarrassing moment of my life by far. I was in middle school about 10 years ago and basically at the most vulnerable age of my life where everyone was trying so hard to be cool and accepted in the eyes of their peers. My mom had a lot of older sayings that I would hear a lot, and some of them rubbed off on me.

One of those sayings was “being fingered” when someone would flip her off. She was fond of saying this in traffic whenever she’d cut anyone off. I didn’t know it meant anything other than giving the one finger salute. You think you know where this is going, but it’s so much worse. Soooo, one day I was walking in a very crowded hallway after lunch and trying to be a cool girl and whatever.

All of a sudden, the most popular guy a grade above me bumped into me while running towards his locker. I yelled at him to watch where he was going, but in a joking manner, more to get his attention than anything else. Well, he turned around and flipped me off. And to get the attention of everyone else and to brag that one of the popular boys had noticed me, I shouted, “Hey! Mike fingered me!”

Bro, everyone and their moms stopped and turned to look at me and laugh. Mike looked upset and ran off. One of my friends pulled me to the side and told me what “fingering” meant. I immediately ran to the bathroom crying and refused to come out. I was then dubbed “finger girl” for the next few weeks until someone got beat up and that was considered more interesting.


6. Sounds Like He Made You Disappear

So, it just so happens that I completely ruined a magic show once. The magician said he needed a good kid to volunteer to come up and help him out. I declared myself a good kid and walked up on stage. Then I made him regret it, big time. I ruined his entire trick by pointing out that the ball he had made disappear was behind a table. He sent me away.


7. Swing Batter Batter

Let me just start this post by saying that I was not a very smart nine-year-old. There was an old wooden play set in my backyard when I was a kid. I don’t remember exactly what happened to anger my dumb nine-year-old brain, but let’s just say I fell off of the play set. Instead of dealing with the situation calmly and maturely, I decided to blame the play set itself for my own incompetence.

I decided to take my anger out on it. I grabbed a metal baseball bat that was laying close by. I put my arms above my head and swung the bat downwards towards one of the play set’s ladder rungs, as hard as I possibly could. I did not win. The metal bat came back toward me and hit me square in the middle of the forehead.

I laid there unconscious for a while and, when I woke up, I had a huge lump where my forehead used to be. That lump stayed with me for a long while after that, as a constant reminder of my defeat for the next few weeks. So yeah. I knocked myself unconscious with a metal baseball bat because I got mad at a wooden play set in my backyard…


8. The Sound Of…Something Other Than Music

I was in a choir when I was a kid. On one occasion, I had an upset stomach, so I was lying down while everyone else was practicing their vocal exercises. The adults all thought that I was faking the illness to get out of having to practice, so eventually they made me get up and sing with everyone. My worst nightmare happened immediately after.

A few minutes later, I puked all over another kid’s head. They let me go home after that.


9. Paul Fart, Mall Shopper

I pooped in my pants at the mall as a six year old girl. I had accidentally farted in the shoe store, and my sister thought that this was absolutely hilarious. “Again!” she exclaimed, as I forced a follow-up fart out. In complete stitches now, “Again!” she cackled. I complied with another loud one. She was laughing so hard that she was nearly in tears.

She shouted: “Again!!!!!!” This turned out to be a request that we would all regret. The point of no return in what was already a horribly unpleasant situation for anyone else around us. Although I no longer had any gas in me, I pushed as hard as I could, determined to make my sister laugh even harder than she already had at this point.

Then, a moment too late, I realized that I was in the process of pooping myself. I can only assume that my sister would have been filming this whole incident on her iPhone, had they been available back in the 1990s. I’m pretty glad that they weren’t. I never would have been able to live that moment down if it had gone on the internet for everyone to see.


10. Unanswered Questions

The most embarrassing memory that I have of my childhood, by far, is of the time when I peed my pants in the middle of class because I thought that the teacher would yell at me if I asked to go to the bathroom. I was pretty little at the time and I’m sure my classmates have all forgotten about it, but I still cringe every time I think about it.


11. Deep River

My most embarrassing childhood memory is walking onto the mud after they had half drained the Lynn River. I fell up to my armpits in mud and had to be rescued by the fire department. By the time the firefighters got me out, there must have been between 50 and a 100 people standing around and casually watching my dumb self get pulled up from the mud.


12. I’ve Got Your Back

One time, when I was a kid, I was at the airport after a long trip with my mom. I hadn’t seen my dad since I got back and was really excited to be seeing him again. While there, we saw a guy with a blazer that looked just like my dad’s. So, without giving it a second thought, I ran over and jumped straight onto this random stranger’s back as he was looking for his luggage.

He must have been so confused!


13. Ain’t That A Kick In The Head

Back when I was a young lassie, I was once trying to impress my crush by showing him how high I could kick. In the process of doing so, I accidentally slipped and broke my wrist. It was pretty darn embarrassing. I’d say my attempt to impress him failed pretty drastically, and if social media had been around back then the video definitely would have made the rounds.


14. Agent Of Chaos

I had, and still have, terrible eyesight. I always had to wear glasses as a kid, as did both my younger brother and my younger sister. One of the times my cousin visited us, he said he wanted to wear glasses too, so he asked us for an idea that could make him need glasses. My suggestion was horrific. I told him to try peeing in his eyes, as it would probably make things blurry.

My cousin then proceeded to emit a vertical stream of urine into his own face, successfully having the better part of it land in his eyes. He never got glasses, and this incident is still brought up at almost every family gathering we have. Oh, and I once, at a very young age, told my even younger brother there was chocolate in the yard left by our dachshunds.

It was not chocolate, and I knew it. Yet another thing that is still brought up at almost every family gathering. Looking back, I was a pretty bad kid…


15. No Time Like The Present

When I was about six or seven years old, I was once wearing overalls and standing in the foyer of my house. Suddenly, I had a massive urge to take a poop. Although the washroom was literally just a few feet away, a bizarre urge overtook me that I couldn’t resist. I started to stand still and take a poop right then and there.

The log slithered out of my underwear and rolled down my pant leg, straight onto the floor. I looked at it, walked away, and then acted like nothing ever happened. No shame.


16. Stupid With A Burning Passion

During recess, a “friend” once coaxed me into throwing a firecracker into the bushes. Which I did, because I was stupid that way. It was an instant catastrophe. The bushes immediately caught on fire and burst into flames. The bushes were also very close to a bunch of residential houses. We didn’t know what to do about it and no teachers were around, so we just went back to class as soon as the bell rang.

15 minutes later, I could hear the fire engines outside the window. Five minutes after that, my “friend” and I were called into the principal’s office. After a stern talking to, several officers had arrived and we were taken down to the station for questioning. Once we were there, we had to explain ourselves again. Ultimately, we each had to do 20 hours of community service.


17. What’s Bug-ging You?

I once had a stomach bug back in middle school and the freaking nurse didn’t believe me. I may have cried wolf a couple of times before, which didn’t exactly help my case. I suffered through school all day until finally, my last period arrived. We were taking a test and I asked my teacher if I could step out to go to the bathroom. Before I could finish speaking, the worst happened.

I projectile vomited right over her shoulder and mostly into the trash can. The jock in the class was like, “Woah, your throw up looks like Sprite!” And even in my stupor I was like, “What the heck?” My teacher then made a girl walk me to the nurse with the soiled trash bin, and the girl was actually super cool about it. She told me not to be embarrassed and took my mind off it by talking about horses.


18. Row Row Row Your Boat

My most embarrassing childhood memory is of that time when I was rowing my younger brother around in our little dinghy and insisted that it should be me, not him, who should hold the duck’s egg that we had found in an abandoned nest. I held the egg between my skinny legs as I rowed us back. Things did not end well for anyone involved…

To make a long story short: The egg rolled off the bench and broke on the dinghy’s bottom. It turned out to be a rotten egg, and the stench was intense, to say the least. I remember literally crying as I was made to scrub out the dinghy while my brother was enjoying his quiet evening meal with my parents. A classic parenting moment, in my humble opinion.


Most Embarrassing Childhood Memories facts | Factinate

19. A Fond Farewell

This is kind of a sad example of an embarrassing childhood moment, but before my grandmother’s body was buried when she passed, one of my aunts kneeled and put her hands on top of her casket to pray. My grandma’s casket had a clear window at the top of it. I was around nine years old at the time, and I saw what my aunt was doing, so I wanted to copy her and do the same thing.

I wanted to pray for her as well, so I got down and tried to do the same thing that I saw my aunt doing. Everything crashed down from there. When my elbows were on top of the casket, the glass shattered in front of the whole family and I cried, thinking I had disgraced my nana’s memory. The moment was pretty emotionally scarring.


20. All In The Family

I’m not sure exactly how young I was at the time, but at some point when I was a kid, my family was on a road trip. During said road trip, my dad had done something to thoroughly get under my skin. I don’t remember what it was exactly, but we were both pretty upset about it and he wanted to fix the situation so that it wouldn’t ruin our enjoyment of the rest of the trip.

He asked how he could make it up to me, and I still to this day cannot explain or forget the response that I gave. I guess I had just heard the expression “family jewels” for the first time on some show, and I had no idea what it meant. So, for no good reason, I told my dad that he could make it up to me by passing on the family jewels to me.

I literally thought there were actually jewels somewhere that every family had hidden away or something along those lines. I didn’t have any clue that I was asking for my dad’s you-know-whats. I will never forget the look on his face for as long as I live. Nor will I ever forget the level of embarrassment I felt when I realized what I had inadvertently said.


21. Dirty Dancing

In fifth grade, I was in a school musical production where in one song I was the “boogie woogie reindeer,” and during the song I was supposed to dance. Well, I ruined it in the most embarrassing way imaginable. My mom had just shown me the movie Coyote Ugly, so I thought the best course of action was to dance like the girls in that movie.

I’m sure there’s still a home video out there somewhere of the fifth grade boy dancing like a stripper…


22. Not Your Typical Chaperone

I’m a girl. One time, many years ago, we were in New Orleans for a college organization conference. I worked in a department at the college I went to and we took some students with us. It was the weekend after Mardi Gras, so things were still pretty rowdy on Bourbon Street. I was newly 21 and there were a couple of 18-year-old girls with us, so I thought it was the responsible thing to stay sober.

I was doing my best to watch after the girls and make sure that they didn’t get themselves into any kind of trouble. It pretty much sucked. I was trying to wrangle one of them by her belt loop when the other talked the door guy into letting her into a strip club. With no other choice, the rest of us reluctantly followed in after her.

The 18-year-old who had dragged us in was having the time of her life, with lap dances and all, and embarrassingly laughing her butt off. My boss is in the back trying to find some way around the whole thing. I’m sober and being grumpy, just waiting for the night to be over with. A woman asks if I can join her on stage to play along with a strip tease or something and she says she’ll get me a drink if I do.

Against my better judgement, I said yes. After all the stress I was under, I needed one! So, I obliged. She walks me on stage and sits me down on a chair. She proceeds to take her clothing off and give me a lap dance, and I’m oooing and aaahing in front of everyone. I’m making a huge deal out of showing how much I love her various body parts because I’m all in for getting this darn free drink.

Then, she grabs my thighs and throws my legs to the side, full on spreadeagle. It all unraveled at that point. The buttons down the back of my pencil skirt immediately rip right off. Now, as unlucky as I was, it just so happened that on this particular day, I was wearing zero underwear. My private area was on full display to the entire club.

Everyone began hootin’ and hollerin’. Finally, the performer finishes her show. I rush off of the stage, trying to pull my skirt down enough past my butt, and trying to button back up whatever is left of it. Completely mortified, I get my free drink. My boss is in the back, just shaking his head, laughing, and he motions me to come over.

He says, “Hey, buddy. Me and you just bonded. I just saw your freakin’ beaver.” The weekend goes on. My cohort lovingly nicknames me Beaver, which eventually evolved to Beazy. I later hooked up with a guy from another school, and left with the nickname Sleazy Beazy from the Big Easy. I tend to think of this extremely embarrassing incident as the end of my childhood and my formal welcome into the adult world.


23. When You Gotta Go, You Gotta Go

When I was a kid, my family moved houses, and it took me a while to get used to the change. In the new house, my brother’s room was where the old bathroom was. So, sadly, on one occasion shortly after we moved in, I absentmindedly sleepwalked into my brother’s room in the middle of the night and peed right in his face. I will never live it down…


24. Smell Ya Later

My most embarrassing childhood moment was probably that time that I went into school with my pants smelling of damp. I actually didn’t know that not drying out clothes properly would cause such a putrid odor. I thought my mom had washed them with my dad’s socks. So, I sprayed what may as well have been a full can’s worth of lynx on them and just went into school.

Wow. The smell was even worse than I ever could have imagined, and way worse than it would have been if I had just left them without spraying the fragrance. Walking down the corridor, I heard someone scream “OMG, WHAT’S THAT SMELL?” and I instantly knew it was me. I ended up pretending to be ill and going home at break time, which wasn’t soon enough.

I will always be thankful to that office lady for letting me go even though I clearly was just leaving because of my smelly pants.


25. Bird Brain

When I was about 14 years old, my family went to the zoo one time and a large male ostrich outrageously flirted with me, doing a full mating dance, leaning back, crouching, and flailing his wings in the air. My family and family friends witnessed the maniacal monochromatic male and nearly passed out from laughing so hard. I was mortified. Fortunately, I never saw him again.


26. The Big Screen

My friend and I thought it would be “fun” to recreate the film Jackass and title it “Jackbutt.” We were something like 11 or 12 years old at the time. But it got more embarrassing than that. Instead of doing anything actually dangerous, we would take the wheels off our skateboard and do stupid tricks on a trampoline, then make a hand signal and yell “Jackbutt” at the camera.


27. Investigating The Evidence

When I was around four years old, I would get cheeky often and do things that I wasn’t allowed to do. When my parents asked me if I did something, I would lie, but it would be very obvious. When they confronted me about it, I asked how they knew. My mother said that a big, red circle would appear on my forehead whenever I lied.

Afterwards, my parents asked me again if I did something bad. That’s why I came up with my “genius” plan. Me, thinking I was fooling everyone, would facepalm my forehead and deny everything.


28. No Mustard?

My most embarrassing childhood moment was the time where I drank an entire bottle of ketchup and proceeded to throw it all up right away. My mom immediately walked in while it was still in the midst of happening. Then the situation took a rapid twist. She thought I was vomiting blood, so she freaked out and started screaming.

I was maybe three years old or something like that, but I still remember this vividly.


29. Dance Dance Revolution

In our spare time back when we were kids, my friend and I used to choreograph dances for various songs, with “Barbie Girl” being one of our favorites. We would then perform the dances for our parents and record the performances on her father’s old video camera. I hope to all that is holy that no one ever finds those old video tapes…


30. A Reasonable Assumption…

I will never forget the time I got my period for the first time at the tender age of 11. It was like something out of a nightmare. Someone pointed out that there was blood on my skirt and I didn’t yet know what that could possibly mean. I went to the bathroom to see what was happening and immediately ran out screaming that I was dying. Everyone around me saw. Good timesss!


31. Cry Me A River

For some unknown reason, my mom had an extremely disturbing habit when I was a child. She took a lot of pictures of me crying when I was young, and she loved showing them to all of her friends. I was a teenager when I found them, and even then I was all like “What the heck, mom?” I am positive that they would all be on social media if it had been around when I was a kid.

It was complicated. No, I do not know why she did it. I do know that I received the least of the questionable interactions with her out of all my siblings. I prefer to think that I was a beautiful toddler who cried gracefully. But deep down, I do worry about some other, unknown compulsion that she has for doing the stuff that she does.


32. Going Down With A Bang

My most embarrassing childhood memory is of the time when I decided to try and cut my own bangs. It was bad. Real bad. I couldn’t show my face anywhere for weeks. I sincerely hope that no photos of the result exist anywhere, or I would have to go to whatever lengths it took to destroy them. Please learn from my mistake and don’t ever try this for yourselves!


33. The Birds And The Bees

In my first ever middle school health class, we were talking about what happens when you go through puberty, starting with girls. A girl from the back of the room raises her hand and says: “You get breasts.” To my eternal shame, I raised my hand and asked the dumbest question ever. “What are breasts?” The whole class stared at me in shock.

To explain, I was very isolated as a child. We had no television at home, and the word “breast” just simply wasn’t in my family’s vocabulary. Plus, this was shortly after I had switched schools and learned the language of my new community. But let’s not kid ourselves, if this had happened today, it would have been all over social media regardless.


34. Coming In Handy

When I was around eight years old or so, I saw a men’s washroom urinal for the first time. It was inside a McDonald’s restroom while my family was having lunch. My reaction still haunts me to this day. I thought to myself, “What a weird sink” and proceeded to wash my hands on it by literally smearing my hands on the surface of the urinal where the water flows.

I got back to our table and told my mom about it. Up until this moment, I didn’t know that it was possible for someone to gasp, laugh, cry, and be embarrassed all at the same time. I’m pretty sure other people from surrounding tables overheard me when I said it. Social media wasn’t really used back then, but if it had been I would have been screwed forever.


35. Is It Raining?

When I was a kid, I once thought it would be funny to pee down from the top of my house’s staircase in the middle of the night. Well, my parents woke up and caught me in the act. They were very confused, and did not find it the least bit funny. Looking back on the incident now, I have no idea what made me want to do it and I am extremely embarrassed to think that this really happened.


36. Too Cool For School

Exhibit A: A 13-year-old male me, wearing a spiked choker, spiked leather gloves, and a Green Day hat, purposely tilted to one side, over my eye. Exhibit B: Me and my friends at a restaurant, me needing to take an awful diarrhea poop, taking said poop and wiping my butt with my underwear. Exhibit C: One of my friends finding out about this and trying to take a photo of the underwear.

I had to sprint, grab the underwear back from him, and hurl them into a nearby field. In hindsight, I have absolutely no idea why any of this happened. It’s extremely embarrassing every time I remember it.


37. The Power Of Love

My mom was in college when I was a baby, so sometimes she’d have to take me along with her to class. Well, one time, we were in the computer lab during finals week back in the age before autosave was a thing. I guess I got away from her by crawling under the tables. I found this nice glowing switch under there and apparently wanted to give it a press. This led to complete disaster.

All of a sudden, as soon as I pressed the switch, the entire lab’s power shut off and about 30 or so people lost God knows how much work. She rushed me out of there, totally freaked out, before anyone got an idea as to what had happened. Even though I was too young to understand what I had done, I cringe every time I remember that this actually happened.


38. I Scream For Ice Cream, Literally

My most cringeworthy and embarrassing childhood memory is of the time when I was three years old and I started chasing the ice cream truck down the street in nothing but my undies, yelling “WAIT! MY MOM’S GOT MONEY!” I can only imagine how ridiculous and awkward this must have looked to the entire neighborhood…


39. Swingin’ On A Star

When I was in the second grade, I once got stuck in a baby swing at a playground. Oh, my misery wasn’t over. The fire department had to be called in to rescue me, and the first responders used the jaws of life to cut me out of it. I am so glad that Facebook didn’t exist back then, or I’m sure that one of the adults present would have posted pictures of the incident online.


40. Ring Of Fire

I once accidentally started a fire and burned my family’s house down to a crisp when I was about four years old. The local news channel attempted to interview me, but I would only say one utterly mortifying phrase. “I like fire.” My brother had to pull me away from that situation as fast as he possibly could. It is definitely the most embarrassing and cringeworthy thing I’ve ever experienced.


41. Say It With Music

My most embarrassing childhood memory is, after receiving the CD as a gift, singing the entirety of Boyz II Men’s “I’ll Make Love To You” on my eighth birthday to my parents, aunt, uncle, and both sets of grandparents, one of which is very religious. “Throw your clothes on the floor, I’m gonna take my clothes off toooo…”


42. A Prickly Situation

My most embarrassing childhood memory of all time is of myself tripping knees-first into the cactus display at a botanical garden. It was literally like something straight out of a cartoon. My mother had to constantly pick the needles out of my knees for the next several weeks. Stay away from those cactuses, kids. They’re bad news!


43. The Letter Of The Law

My most embarrassing childhood memory is of losing the Arizona State Spelling Bee and coming in third runner-up. I was twelve, and the word was “genuine.” I spelled it correctly, but due to my accent and speech impediment, the spelling bee judge heard me say “J” when, in actuality, I said “G” as the first letter. I felt like everyone watching thought I was a huge idiot.


44. It’s Not Where You’re Going, It’s How You Get There

At the age of 14, I once accidentally peed in my pants while I was riding in the back of a cab on our way back from hanging out at a local school that we snuck out of our dorm to visit. It was not a pleasant experience. The ironic touch for me, though, was that I was living in a dorm at a college in Virginia instead of going to high school, because I was in a “gifted” program.

Yeah, I was gifted. Gifted with a complete lack of common sense!


45. Taking It Out On Their Skulls

When my cousin and I were both around kindergarten age, she once accidentally busted my head open with a rock because she was mad about the fact that I was standing on her favorite rock without permission. It was some straight-up baby neanderthal stuff. We all laugh about it now, but I was embarrassed beyond belief about it when it first happened.


46. A Fugitive Still At Large

One time when I was a pretty young adolescent, I went out in public barely dressed one night and I thought that I was going to get into some big trouble when a nearby officer spotted me and came over to ask me some questions. So yeah, my most embarrassing childhood memory would have to be running from the officer wearing nothing but Doc Martens, a Costco hat, and a cast on my right hand.

In the process of running away from him, I remember jumping a fence as best as I could, only to catch the toe of my boot on a picket and fall directly into some fitzer bushes. I then remember getting myself untangled only to fall into some more fitzers in the exact same yard. But somehow, the officer never saw where I had landed. As a result, I got away.


47. An Important Part Of A Healthy, Balanced Diet

When I was a really small kid, as in roughly toddler age, I was in love with a toy red plastic tomato from a grocery playtime type toy set. I always took it along with me to every single place that I went. To be fully honest, I don’t remember this whole thing too vividly. But everybody in my family thinks it’s absolutely hilarious and will never let me live it down.

They love the fact that, unlike most other kids, I didn’t have a blankie or a teddy bear, I had a red freaking plastic tomato. To this day, I get given some version of a red plastic tomato by at least one member of my family at almost every single gift-giving occasion I attend. The three words “red plastic tomato” have become meaningless to me now, since I’ve heard them so many darn times.

Needless to say, this will always be my most awkward and embarrassing childhood memory.


48. Princess Charming

I’m a male. Back when I was six years old, I once had a heated argument with my female next door neighbor. The argument was about who would get to be the princess in the game of pretend that we were playing. She refused to back down, and we had an adorably heated argument over the matter. In the end, I rage quit, declared myself to be Queen of the World, and flounced off to find something else to do.

My mother wrote the date down on a calendar and still has the calendar 18 years later. She never wants to let me forget that this embarrassing little incident really took place.


49. Dancing Like The Rest Of Your Life Depends On It

When I was four years old, I was a flower girl at my uncle’s wedding. They had an excruciatingly long ceremony, during which I had gradually gotten pretty bored. So, I absentmindedly started pole dancing with a column that had a statue of the Virgin Mary on top of it. I have no idea how I knew what pole dancing was, but I’ve seen the old beta max video of the incident.

It’s pretty impressive. I think I missed my calling in life. Either way, no one in my entire extended family is forgetting this incident any time soon…


50. Coming To The Rescue

My most embarrassing childhood moment was giving the Heimlich maneuver to the wrong actor at the wrong time during a school play. He also wasn’t even choking, but I insisted that he was choking while I repeatedly gave him the Heimlich. He was just talking to someone onstage while I came out of nowhere. Everyone, including the teachers, was rolling on the floor in laughter.


51. A Simpler Time

I’ve said it before and I will say it again. I thank God every single day that social media was not a thing until after I had already graduated from college. Growing up without social media was the best. When you left school, all your school problems stayed there. There was no cyber bullying. The most you had to deal with was someone calling and asking if your refrigerator was running.

Or someone calling you up and doing a Bart Simpson, asking to speak to I.C. Weiner or something like that. As for what I would be embarrassed for, I’ve got two words for you: Butt Cut. I have no idea why I thought that haircut was attractive as a youngster, and I will do whatever it takes to keep all photos from that period of my life from ever emerging.


52. The Good Old Hockey Game

When I was a 14-year-old boy, I was at my sister’s hockey banquet. There were more than three hundred girls in attendance, who I considered a bunch of babes. As the speaker approached the podium, Don Cherry for all you hockey fans, I was leaning back on my chair trying to look cool. Indeed, as it turned out, I had leaned back too far.

I began to fall back on the chair and grabbed a hold of the table cloth to hang on to. I ended up pulling the entire KFC food party banquet onto my head and lap, gravy included. My elbows also hit the piano keys behind me, making a massive B flat note ring out throughout the gymnasium. Everyone instantly realized that their lunch had been ruined thanks to my antics. Oh, but it got worse.

When Mr. Cherry got to the microphone, he pointed over in my direction and said, “Thank you, Maestro!” I lost a little bit of my soul that day.


53. Ringing You Up

When I was about seven or eight years old, we took a field trip to the Field Museum here in Chicago. It was during our lunch break, and I wandered off to the gift shop to see what they had for sale. I had a huge crush on this girl named Victoria in my class, and I saw that they were selling this ladybug ring for only a couple of dollars.

I knew that Victoria really liked ladybugs, and I had enough money to buy it since my parents had given me money to buy whatever I wanted from the shop. So, I decided to buy the ring with the intention of giving it to her. I was really nervous and kept waiting for the right time to do it. I eventually decided to just go for it and walked up to her near the end of the trip.

She was with some of her friends, which made me even more nervous than I already had been, but I eventually somehow managed to find the courage to do it. Her response chilled me to the bone. When I did, she just looked at the ring and laughed. Her friends joined her in laughing, and she then tossed the ring in the trash right in front of me.

I was completely devastated and tried hard to hold back my tears. Even though I’m over it now, that completely screwed up my confidence with girls for a very long time. Looking back, I may have embarrassed her too by giving it to her in front of her friends, which may be why she reacted that way. I have some amount of empathy for that.

But even still, it makes me cringe whenever I think about it. I can only imagine that with social media around back then, and it happening in such a public and crowded place, there would possibly have been a video posted on YouTube or Twitter of that embarrassing moment. Really glad it was just between me, Victoria, and her friends.


Sources: 1, 2

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