March 23, 2023 | Eul Basa

Humiliating Fails: These Moments Of Triumph Went Totally Wrong


There is nothing so sweet as the taste of victory, and there is nothing so sour as having that triumph pulled out from under you before you could truly enjoy it... We’ve seen plenty of examples before; the birthday cake that slipped from your plate and splattered like a Jackson Pollock painting all over the kitchen tiles, or the premature celebration of the basketball player whose three-point ball ever-so-gently danced off the edge of the rim and out of the basket—how cruel the universe must be to tease us so! While it hurts in the moment, at the very least we come away with entertaining, albeit self-deprecating stories that we can share with strangers on the internet.


1. This Way Out

I tried to dramatically leave and slam the door after an argument in a new apartment. I walked into a bedroom...

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2. Feeling Good, Looking Better

After losing some weight and getting over some shyness I decided it was time to put on a black dress, heels and head out. As I walked to my car, a group of guys driving by honked their horns. They all waved and whistled and I thought...wow maybe I am looking great. So naturally, the next thing that happened included me tripping in my new heels and face-planting in front of them.

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3. Going Up

I had a triumphant moment where I told off some girl for being a jerk, then I swung around and pressed the up button on the elevator. After five seconds of waiting, I realized she was still behind me, so I considered taking the stairs instead. As I walked towards the stairs, the elevator door opened. I went back to the elevator, red-faced and awkward, and had to stand there for another five seconds until the door closed.

We made eye contact. It was weird.

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4. Walk the Walk

My eighth-grade graduation. It was my turn to take the stage to get my diploma. I grabbed it with one hand, shook the principal’s hand with the other, and didn't notice the stairs—I walked right off the side of the stage. I wasn't seriously hurt, but it was super embarrassing.

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5. Independence

I had just told off my ex-boyfriend, who had been trying to tell me I had become too dependent on him and wouldn't be able to leave. "Screw that," I said, "I am independent. And I don't need you for anything!" Then I dramatically turned to get into my car and drive off...but I had locked my keys inside. Oh, but it gets worse.

The car was still running. I felt like a complete idiot. He had to call and pay for a locksmith because I had no cash and the dude didn't take cards. I will never forget that grin on his face. Dumbest moment of my life.

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6. The Collage

The first day at my new job was a Friday. I was super pumped. When I got there, I put up pictures in my office, including a huge collage of pictures my girlfriend had made for me. I get lots of compliments over the course of the day while meeting new coworkers cause she's pretty and people were surprised I got the job. Feeling like a million bucks.

Go home for the weekend. My girlfriend breaks up with me. I have to explain the whole next week why I took the photo of my girlfriend down...

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7. The No-Doubter

I hit my first ever home run in high school and I knew when I hit it, it was gone. We always practiced what we'd do if we hit a no-doubter, so in the split second I had to show off, I flip the bat. The bat flips end over end, hits home plate, then straight up in my face. I was unconscious for 15 minutes and since I couldn't run the bases, they called me out.

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8. No Cigar

I was carrying a large tray covered in full cups of hot drinks when I tripped on a tea towel someone had left on the floor. Somehow, I slammed myself sideways into the wall before falling right over and I managed to keep all the drinks upright. I stayed there for a moment, balanced up against the wall, not able to believe my own luck when I slowly began to slide downwards.

Both hands were needed to keep hold of the tray, so I desperately shuffled my feet trying to get some traction, but I got nothing. I hit the floor and sent every drink flying.

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9. Walking Out

I broke up with my girlfriend of three years after a long talk in her room. I was sitting in her desk chair in an awkward position while she was sitting on her bed. After the breakup was done, she was bawling. I went to stand up to walk out, and the second I put any pressure on my legs I immediately collapsed. I guess they fell asleep over the lengthy breakup talk.

We both started hysterically laughing. It definitely lightened the uncomfortable mood. Not one of my finest moments.

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10. A Son in Need

I got into a nasty fight with my dad when he was talking down to me and coming across like I couldn't make my own life decisions as an adult. So, I managed some comeback and left the house. I go to get in my car and drive away, and the darn thing broke down a quarter mile from our house on a hill. That's when I had to call him to come and help me.

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11. V for Victory

I was running my first marathon and it was grueling. I had my name written on my top, so as I was headed toward the last mile, people were chanting my name, strangers cheering me on, my parents were there...it was euphoric. Until the moment it wasn’t. I crossed the line with tears in my eyes and threw my arms up to yell and cheer.

Instead, I burped/vomited all over myself.

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12. The Breakup

A few years back I dated a guy who was, to put it simply, a jerk. He was very mean with his humor, had a lot of anger issues and was very critical of everything I did/said. Overall, it was just a very unhappy time in my life. I stayed with him hoping things would change—I'm sure most of us have made that mistake before—and after realizing that it would never happen, I decided to finally break up with him.

So, went over to his apartment and since his roommates were home, we went outside to the parking lot to talk. That's where I explained why I was breaking up with him, and the more I talked, the angrier and more passionate I got. I'd imagined saying these things to him for forever, so the words came out eloquent, natural and powerful.

I could see he was feeling guiltier and guiltier, which is exactly what I wanted. Finally, I finished my speech, gave him a moment to say something, then began to walk away when I realized he wasn't going to. I was trying my best to look good as I walked back to my car, but a dip in the ground caused me to trip and I ultimately face-planted into the concrete.

I ended up spending the next hour crying in his apartment bathroom cleaning up my scrapes.

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13. Cat-like Reflexes

After a lot of beating around the bush, I finally convinced a cute girl to go on a date with me. It was, however, the dead of winter, so when she arrived at my apartment, we mutually agreed to hang out on my couch, watch a little TV and enjoy a couple of beers to insulate ourselves from the onslaught of cold we'd have to endure to go anywhere that wasn't my apartment.

After a couple of beers and a couple of episodes of Scrubs, we decide we're ready to brave the cold, and we make it exactly one step out of my building before we decide that it is entirely too cold for the walk to the restaurant we had originally planned on eating at, so she asks if maybe we could just get a burrito at the shop I managed—which was nice convenient, one block away, and then maybe we could stay in and play video games.

Score. I love this plan. I love this plan so much I want to dump the girl making it so I can marry this plan. We pop our heads into my workplace, get enormous burritos and drinks for a hugely discounted price, and then trudge back to my apartment. As we're on the walkway up to my building, I shift my burrito into my right hand so that I can rummage through my pocket for my keys with my left (I'm left-handed).

As I look up, I see it. My date is about to try to walk over a huge patch of black ice on my sidewalk that can't be seen in the dark of night. On cue, she slips and flings her burrito skyward, but since I was a step ahead of the disaster, I catch her with my right arm—without dropping my burrito or my drink—and gracefully snatch her dinner midflight with my left hand, and then prop her upright. Bingo! Disaster averted!

She's thoroughly impressed with my catlike reflexes and my gentlemanly dedication to the well-being of her person and her dinner. She gushes for a second about how cool that was, I told her I knew the ice patch was coming, and to look out for the second one a few steps ahead—I knew they were both there having had to avoid them in the daylight—and she gingerly bounces over it, turns to give me more praise and then...

I immediately slip and fall on the second ice patch I explicitly warned her about, hurling my drink, and both burritos into the air. She doesn't catch any of them. I hit the back of my head hard enough to bleed, and instead of spending the night eating junk food and playing games with a cute girl, I spend the night on the couch trying not to vomit from disorientation into her lap.

...Yeah, so maybe that didn't turn out so great.

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14. Down and Out

Not so much a moment of triumph; more so snatching adversity from the jaws of defeat. I was cycling home, tried to mount a curb, got the angle slightly wrong and flew artlessly over the handlebars, landing painfully in a crumpled heap in front of a crowd of commuters at a bus stop. Most of them guffawed mightily, though one, one asked if I was OK.

As nonchalantly as I could, I made light of it—happens all the time, it's no problem, I'm fine, and swung myself back in the saddle. Well, my nightmare wasn’t over. Failing to notice that the handlebars had turned 180° and the front wheel was a mess of tangled brake cables, I applied a mighty downward shove on the right pedal and promptly fell off again.

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15. Cause for Celebration

As a teenager having completed my first solo flight in a glider—I was an air cadet and the first solo is a HUGE achievement—I jumped out of my now safely landed glider, raised both my fists in the air and screamed out in joy. Sadly, in Air Cadets flying operations raising both your hands is a signal that you saw something dangerous. As soon as I did it everyone started screaming, "STOP FLIGHTS, STOP FLIGHTS!"

The tow plane on the ground shut its engine down, all gliders were pushed back to their parking spots and I got yelled at for a while.

Ruined Moment of Triumph facts Pxfuel

16. The Contest

I have to go back to high school for this. I am, and always have been, quite skinny. One of my buddies was bragging about how many pull-ups he could do. I asked how many, and because it was high school, people were impressed when he said "Eight." That was a high bar for some reason. Anyhow, I replied that I could probably do more, not really knowing how hard it could be.

This was jeered, booed, and generally mocked. Eventually, a contest was set up in the gym. After he cranked out nine pull-ups, I took my turn. It was tough, but being thin really made it pretty easy. I got to 10, and immediately his girlfriend pulled my pants down. The tighty-whiteys I wore that day had a nice, gaping hole, right above the butt.

The nickname "Whiteys" still sticks with me among those people, to this day.

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17. Sticks and Stones

It was my freshman year of college, and my then-girlfriend and I were at the end of our relationship. Although neither of us had admitted that we actually broke up, which resulted in many nights of hooking up only to regret it the next day. It was really emotionally damaging for both of us. After getting some attention from a cute girl in my English class, I decided that we should finally end this relationship, or else we'd be stuck in a loop of love and hatred forever.

So, after class, I go to her dorm to talk to her. Her roommate is there with her, so instead of asking her roommate to leave, we go talk in the hall. Now at this point, I think I should mention her dorm was on the second floor of the hall. So, we talk for close to an hour, and finally, I tell her that it’s best if we just finally break it off.

We're both in tears, seeing as we were together throughout most of high school, and here we are ending our first real relationship. In that blurry haze, I turn around to make my descent down the stairs, only to misjudge the height of the first step. So, I go tumbling down the stairs, breaking my arm in the process, resulting in the girl I just broke up with having to drive me halfway across town and waiting with me for three hours in the ER.

Somehow that wasn’t the worst part. How? Not a word was said between us the entire time.

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18. Leaving the Nest

When I left home, I pretty much came and got all of my stuff in the middle of the night. The only thing I had left to get from home was my bed. I came back with a few people and my mom was home. She starts screaming at me per usual and for the first time, I screamed back. I unloaded everything on my mind, and it was so liberating.

As I turned to leave the room I tripped over my feet and fell smack into the wall, face first. So anyway, I know what it is like to have clumsiness derail your victory moment.

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19. Dunking Like Jordan

When I was a sophomore in high school, I was playing in a basketball game. I find myself in the right place, at the right time, and steal the ball. Then I experience an amazing adrenaline rush as I charge to the basket uncontested. Finally, I leave the ground, everything goes silent. Engage slow-motion epic life moment.

I soar through the air like something from an old Jordan poster. I commence the most life-fulfilling epic tomahawk-dunk ever imagined by a 15-year old. Real-time re-engages, as does physics. I land uncontrollably, and completely slam into a pack of cheerleaders standing just out of bounds. Four cheerleaders went down. Two cried.

So much for my moment of glory.

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20. The Competition Swimmer

I used to work at a very popular beach as an ocean lifeguard. So, I got introduced to this job because I was a competitive swimmer in high school, and my coach wanted me to keep swimming for the summer off-season. While I was small and skinny compared to all the other guards there, I was also an extremely fast swimmer and runner, and could out-perform many of the guards on the beach when it came to endurance and speed.

During the first week of the job, the guards learned my name and wanted to see how fast I actually was. So, one morning for workouts, some of the guards told me to race to the buoy a few hundred meters out. In my head, I was thinking—no sweat, I'll just sprint to the buoy and show them all that my speed makes up for my size.

So, to show off my competition swimming prowess, I ran from the beach and dived into the cold ocean water. Except, the beach shore isn't like a swimming pool, and it's shallower than it looks, so I ended up face-planting into the salty, wet sand, in front of all the guards. It was a painful swim too...I had sand cuts all across my face, and the salt didn't help much.

Ruined Moment of Triumph facts Peakpx

21. Rubbing it In

My ex was a bartender at my local watering hole. She had recently dumped me for some loser. I wasn't going to stop going to the bar just because she was working, heck, I was a regular before she started working there. Her new boyfriend was always around when she was working, so I decided to bring in my new girl who was much better looking than my ex.

The plan was to have my ex serve us drinks all night knowing it would tick her off. After all, screw her, she started seeing someone else before breaking it off with me. She was obviously agitated all night, until one horrible moment. The moment when my new girl throws up right there on the bar. Not from alcohol, she wasn't a heavy drinker. I attribute it to the questionable pub food.

Nevertheless...we walked out with my head hung low.

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22. Poor Choice of Words

There was this cardio bunny who I bumped into last week, I used to hang around with her brother ages ago, and we were in a line together. We got talking about fitness as I recall she was quite sporty. I mention my gym is bad and she says I should check hers out; she mentions her guest pass. I jump at the chance, both for the gym and a possible hookup.

We go, I do weights and she runs on the treadmill, then the cross trainer, then a few reps on the crunch machine for some reason. She asks what am I doing after this; I say might watch a movie, I've got a pirated copy of Avengers I've been meaning to watch. She says she has always wanted to see that, so I maintain my spaghetti and ask her to come, she accepts.

We go to mine; I crack open my cheapest wine, and soon enough we are watching the movie and talking a bit. She is apparently a bit of a lightweight and the wine goes straight to her head. We eventually get talking about adult stuff. Oh god, just typing this hurts...She mentions her ex refused to do one thing with her. I say something along the lines of "What an idiot."

She goes in for kiss, we kiss for about five seconds. She pulls away, then I, for reasons unknown, need to fill a non-existent void with the worst possible thing I could’ve said: "You know, I could give you the old lick-a-roo."I said it jokey and cheeky but there was no way that didn't sound weird. I may have sort of winked a bit, oh god. She looks at me like I am a shoe sniffer, pulls away and says, "Err, yeah, just going to go to the toilet."

This occurred roughly around when the Hulk is smashing up the plane in the movie. She returns and I put my hand on her knee in an attempt to salvage what I can. We make awkward small talk for what feels like an eternity; man, this is a long film. When the Hulk punches Thor I remove my hand from her knee. Eons pass and the film finally ends.

I walk her to my door and go in for a hug, she effectively pats me on the shoulder. I never saw her again.

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23. Forget Me Not

A couple of years after university, I came back to my home city for a visit. I had been living abroad. I got some old friends together for a reunion, and to my surprise, a girl I crushed on throughout high school and university was there and looking smoking hot. So, all night I go about putting the moves on her and it is working well.

She agrees to take me back to her place. In the cab on the way home, I tell her I had a crush on her for years and did not understand how we had not managed to get together before. She then comes back with: "We hooked up in university after junior year...It was during a Halloween party on the steps inside your fraternity house."

After seeing the look of disbelief on my face the next line was, "You don't remember do you." At this point, it was coming back to me, but alas, the damage was done. I was swiftly booted from the cab. I haven’t seen her since.

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24. Read All About It

I once caught fire late in the fourth quarter against our longtime youth basketball rivals, closing the game out with a twisting layup that eliminated any hopes of a comeback they may have had. As their coach called a timeout to regroup, I danced a mocking jig on my way back to our bench, mimicking a taunt their point guard had aimed at us earlier in the game.

Jigging merrily backward towards our cheering section, a teammate ran out to high-five me but accidentally clipped my heel while I was midair, mid-skip and thoroughly off-balance. I performed a sort of wonky front-flip and landed in an oddly suggestive sprawl as my teammate, carried forward by momentum, tripped over me in turn and joined me on the parquet.

Worse still, the game story ran in the local newspaper with an unfortunate headline image which showed me throwing a successful head-fake, the result of which was a defender mounting my crouched, grimacing self, loins pressed firmly to the back of my head. The story may have mentioned that I was the league's leading scorer that season, but, perhaps unsurprisingly, most of the chatter at school the next day centered on my front-page tea bagging.

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25. The Speed Walker

I was on my way to a major job interview at a big media company and I was super nervous. As I got out of the car, I tried to psych myself up so I would exude confidence. I walked toward the building and reminded myself to stand up straight, walk tall, smile and look smart. I was almost late, so I walked a bit faster.

In the process of being straight and tall and fast, the heel of one shoe got caught in a sidewalk crack and I went down, hitting the pavement hard. I scraped the heck out of my hands and my wrist hurt terribly, but my suit wasn't torn so I continued on. When i entered the building, I ducked into the restroom before the interview to pick the gravel out of my palms.

I had to shake hands with six different people and it stung like crazy each time, but I just tried to smile and stay confident. The next day, I had to go to the doc and get x-rays and a brace for my slightly fractured wrist. I did get the job though.

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26. Comeuppance Received

We had this one friend, "Mary-Ann", that would just be a general jerk to everyone for no reason. You know the type—insecure, domineering, sports champ, no tact or inhibitions whatsoever. She would choose a different girl to pick on every week, and this week it was my friend "Haz." Mary-Ann was going on about how Haz would probably never get a boyfriend until she lost weight and grew her hair and got "less ugly"—you know, really constructive, friendly advice.

Haz lost it, which was brilliant. We all wanted to see Mary-Ann get her comeuppance. Haz stood up and just let rip about how she was a spoiled little brat and she couldn't just say whatever she wanted and none of us like her anyway, so just screw off, Mary Ann!! Haz, red in the face, swiped her bag off the table and went to march out, promptly tripping on a chair and falling flat on her face.

There was a horrible slapping sound as skin hit hardwood. She was literally sprawled out in front of about 70 kids, who naturally erupted into laughter, Mary-Ann included. To her credit, she managed a weak chuckle; she knew she had to laugh at herself. I got up, grabbed her and pulled her out by her arm, and then spent the next hour consoling her in the girls' room.

We are still best friends and she is newly engaged; happy ending.

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27. Caught on Tape

At a track meet in high school, I cleared my highest pole vault ever in a state meet, then jumped up and down happy to have achieved it. My teammate tapped me on the shoulder to point out that my willy was flopping out of my shorts. All caught on tape.

Ruined Moment of Triumph facts Pixabay

28. Dominoes

Being a nerdy and shy kid in high school, I was never in the “popular” crowd or classified as one of the pretty girls. The school was having a charity fashion show, hosted by a locally based amateur modeling agency. I was approached and asked to be a catwalk model. I eagerly said yes. The night of the show came, I worked that catwalk like a pro, until the final outfit.

All 12 of us wore the same top and jeans, and walked around in a line. I was right at the back. I tripped and fell onto the girl in front of me, who fell onto the girl in front of her, and so on, like dominoes. When I stood up, I got a round of applause, and all the other girls just sat and laughed at me. I was so embarrassed.

I did take a bow though.

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29. Passing the Test

I had just passed my driving test, and I excitedly went straight out to the car to tear down my learner plates. Then I managed to stall the car three times pulling out of the test center parking lot. During this painful procedure, a woman in the car opposite me just watched and laughed. Eventually, I managed to traverse my way out and sped off down the road blushing horrendously in the process.

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30. Jumping the Fire

Last summer, I ran a five-kilometer (roughly three-mile) obstacle course called the Spartan Race. It was held at a ski resort in the summer, at the end of June. I'd signed up for this race as a stepping stone in my weight loss journey and trained really hard for it, so I was really glad to be running that day.

The very last obstacle was a fire pit you had to leap over before you could get to the finish line. I psyched myself up, ran forward, leaped in the air... and somehow twisted my ankle when I pushed off the ground. I managed to land awkwardly and hobble/stumbled my way to the finish line in tears. There was a sports photography company there that day, snapping photos of everyone on the course.

You could look up your "jumping the fire" photo using your bib number on their website. Mine wasn't there... probably because of the agony on my face.

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31. Growing Pains

I was 16 years old, and walking through the mall looking cool. I had some kind of drink with a straw and was leaving to go outside when a group of girls my age walks in through the mall entrance. They look at me as I casually bring my drink up for a sip. That was the moment when the straw stabbed me in the eye.

But it gets worse. I keep walking to get outside and push on what I thought was the door, but was instead the window beside the door and walk right into it, crushing my drink into my chest and getting soaked. I heard some laughter and left; never turning back.

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32. The Rink Wink

I was at a skating rink at a party on Halloween. I skated past a pretty lady who was sitting at a table and I tapped her shoulder as a cruised past. Then, I turned my head as I was 10 feet past and gave her a wink. She smiled and winked back, and I promptly faceplanted and got a bloody nose—having to skate back near her table to get to the restroom and clean up.

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33. Bad Chemistry

It was the end of the semester and we were cleaning out our drawers in our chemistry lab. We had all of our glass pieces out to be inventoried; we would have to pay for anything missing. The girl across the lab table from me had been a total jerk all semester. I discovered I was missing a piece and it just so happened that the piece was in her collection, very near to my collection. She'd slid it over into her stuff, obviously.

I suck at confrontation, but I'd had it with her and let out all my anger and called her a thief. She denied it of course, but I didn't back down and finally, she just gave it to me and let me win the argument. HA! Then I discovered my piece in the back of my drawer... I took a deep breath, apologized, and gave her piece back.

Of course, she wasn't gracious, but she didn't have to be. I was wrong. I stood up for myself, won a heated argument, and discovered I was the jerk.

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34. The Finish Line

I discovered that I could run in my second last year of high school, after being athletically embarrassing my entire life. Like, really run. Faster than anyone in my class. It was a dream come true. At my school athletics tournament, I came first in every race. So, I qualified to run in our regional tournament. Again, I was over the moon.

Fast forward to the regional tournament 200m sprint. I'm at my starting line pumping more adrenaline than should be humanly possible. My classmates are cheering my name from the stand. I can barely breathe. BANG. I'm off. I feel that I'm doing well and I had that sensation you get when you literally cannot throw your legs any faster.

Then I round the bend and watch my competitors fade from my peripheral vision. I'm on the straight now. My heart is pounding. There isn't a competitor to my left or right. I'm coming first! I was the fastest in the region! I decided not to take any chances and dropped my head, staying focused on remaining in my lane and waiting for my finishing line. That line that would bring me so much popularity and fulfillment.

There it was. I threw myself across the finish line and walked onwards in exhaustion, but pride at my success. Then an event organizer walks up to me and hands me my banner. I couldn’t believe my eyes. Third?! How could I come THIRD?! I look behind me. Oh yeah. I had stopped at the wrong line...and then walked across the finish line. Which would explain the gasps of shock from my classmates.

Next year I was back to my slowpoke ways and I never had a chance to redeem myself.

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35. Food Fight

In high school, I sat at a table with my friends from theater arts which happened to be next to a table full of jocks who loved to throw things at us. Usually, we ignored it, but one day they threw a carton of milk that hit my friend in the head. She started to tear up, so without thinking, I flung my entire tray of food like a frisbee and it smacked the guy right in the face with such force that even I couldn't believe it.

As my table rejoiced and I felt pretty good about standing up for my friend, one of the guys from the table told on me and I was taken to the principal’s office as the jocks laughed and made fun of me. And people think the geeks are usually the snitches...

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36. Seeing Stars

This happened when I had just started ninth grade and was crippingly shy. A new school meant new faces, but also new opportunities to change how people saw me. A few weeks into classes, we got a new student in my algebra class. She was an adorable girl, with long dark hair, a slight Southern accent, and gave off a sense of shyness/humility.

The first day she came in she was pretty quiet and didn't seem terribly comfortable after being introduced to the class. I knew how awkward I would be if I were in her position, so I decided to man up and change my hermit-like ways. After class, I caught up to her and tried to put on the impression of the smoothest, sweetest, guy that you can imagine.

I asked which class she was going next and she said she didn't know. I looked at her schedule, lied, and said it was right by my next one just so I could make a good impression and help her out. She smiled and thanked me, and right then I realized I hadn't even introduced myself. I reached out my hand and said, "By the way, by name is—" That’s when it happened.

Right as she shook my hand I walked straight into a wooden post. I saw stars for a second, but luckily, I didn't fall over. From that point, the impression was gone. I tried to keep speaking smoothly, but I kept stuttering out of embarrassment/anxiety, and shuffled the rest of the way to her next class. So, there you go.

Fortunately, it wasn't all for nothing. We became friends, developed crushes on each other, and stayed in contact. We never dated, but it was alright.

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37. The High-Five

I played as a pitcher on an all-girls softball team. We had just won the last playoff game. I caught the ball that was hit by the other team's pitcher! They made us line up and walk across home plate as the head coach (my dad) handed us out our championship trophies. I decided to jump up, give my dad a high-five, and grab my trophy.

Instead, I fell on my butt in front of everyone. The worst part? The popular kid from my junior high was announcing our names on the PA system, and before he even called my name he started to laugh. I almost died.

Ruined Moment of Triumph facts Pickpik

38. The Thing

In my early 20s, I went on a date with a HOT guy who had been a year behind me in school. We met for lunch on a workday. I was charming, hilarious, having a good hair day, etc. We part ways and I'm patting myself on the back for how I rocked that one. I took a look at myself in the rear-view mirror before driving away—you know, to give myself a congratulatory wink—when I make a horrifying discovery.

I see I have the biggest, greenest THING in my teeth known to mankind. Sigh. I never heard from him again. He probably sucked though...

Ruined Moment of Triumph factsShutterstock

39. Blood and Fury

I had found out my girlfriend of two years had been cheating on me with a friend. So, I decided that that was that, and drove over to her house to collect my things and tell her what I thought of her. After getting the few things I had there, I started telling her off, and all of the sudden blood started pouring from my nose.

At first, I thought I was having a brain hemorrhage because of the anger, but it turned out to be from the dry December air. So, I drove home, furious and bloody, and completely embarrassed.

Ruined Moment of Triumph facts Shutterstock

40. The Exit

I worked in a call center as a floor manager. One of the agents on a different team was always complaining and plainly hated her job. She was a terrible employee who was always late but wouldn't quit because she wanted to be able to collect her unemployment. I was outside on a 10-minute cigarette break when I saw the woman come storming out of the front doors.

She had a look of triumph on her face, so I asked her if she finally got fired. She replied with a loud yes and turned around, faced the doors, flipped the bird and yelled screw you at the top of her lungs to the building.  Upon turning around, she walked right into the flag pole, busting her nose and bleeding all over the place.

Most people watched in horror as she gushed blood. I stood there and laughed...

Everyone Quit factsShutterstock

41. Stuck the Landing

I was cycling home after a long bike ride. I was going about 30 miles an hour and was coming to my driveway which then had a large pothole at one point at the base. As luck would have it, I pulled into my driveway still going about 25 miles per hour. I flew into the air and about two seconds later, I landed with my front wheel in a flower bed and my other wheel on the other side of the fence and back near the road.

My bike is in one piece, I'm in one piece, and my friend is freaking out about how cool it was. I jump off laughing; saying I would do it again if I could, and begin to pull my bike out. Unfortunately, I neglected to notice the back wheel was starting to enter the road. About 15 seconds later, a car comes around and at the last second, I notice and jump out of the way—but my poor bike. She didn’t make it.

Ruined Moment of Triumph facts Shutterstock

42. What Goes Up

I was in fifth grade, and the school I went to was across the street from a golf course, so golf balls would end up on the playground. Teachers would try to collect all of them so students wouldn't hurt each other with them. I was standing with friends at the baseball diamond when a couple of bullies walked by and said something smart.

I forget what it was and what I replied with, but I had an amazing comeback and they started to walk away. As a show of victory, I tossed one of the golf balls I had found up in the air and yelled, "See ya!" As they turned around to glare at us, the golf ball came down and hit me in the head.

Ruined Moment of Triumph facts Pikrepo

43. The Compliment

I was once riding my bike down the road, during rush hour traffic. I hopped up on the sidewalk until I could turn on a side street because the traffic was so crazy. There was a really hot guy walking toward me on the sidewalk. He stepped off into the grass while complimenting the tattoo on my chest. I beamed, said thanks, and rode on—only to wipe out five seconds later because some construction debris got caught in my front wheel.

It was the worst case of road rash I've ever had. I picked up my bike, bleeding all down my left side, and limped into a dark alley to cry myself to sleep.

Ruined Moment of Triumph factsShutterstock

44. The Crush

I'd had a crush on my friend for a while. She was pretty, sweet, funny, etc. Anyway, I finally got up the nerve to ask her out. We went to the movies, laughed our butts off and ended up back at her place as I was dropping her off. I leaned in and kissed her. After pulling away, she bit her lip then said, "Maybe we should go out again sometime."

I nodded, agreeing that it was a great idea. Then I turned to walk away, trying to look cute and not like I was freaking out because of the awesomeness inside, playing it cool. Well, I wasn’t really paying attention. What a mistake. I walked right into my car. Caused a pretty bad nose bleed and had to get brought back into her place with blood all over me.

Not my best moment, but the relationship lasted three years!

Worst Thing Done on a Date FactsShutterstock

45. Hold Your Tongue

I'm part of a classical sword combat and historical reenactment club at my school. One day during a one-on-one spar between a friend and I, which went on for quite some time, I had my blade wrenched from my hands thrown off the edge of a balcony. This doesn't count as a defeat until I surrender or he makes contact, so I reached up with the intent of disarming him with a hold on his sword-arm, but he dodged and instead my hand went straight into his mouth and I grabbed his tongue.

I won the fight, but it was really awkward.

Medical Practices factsPixabay

46. Epic Landing

Years ago, I was going with a friend of mine to pick up his small fishing boat that had been in for repairs. We were on an island in northern Washington, and the boat was on another island. At the time I worked for a local air tour company and asked our pilot if it would be possible to hitch a ride on an aircraft of some kind, which would cut the two-hour trip down to about ten minutes.

He not only volunteered but offered to just drop us off at the beach next to the marina. Sweet. So, we come in low over the water, do a quick orbit of the marina, and touch down on the beach just long enough for my friend and I to jump out. It was pretty much a pure epic moment, witnessed by everyone on the docks.

We then proceeded to maneuver our way over to his boat and take off, with the transmission completely self-destructing less than a hundred yards from the dock. We had to return to the marina with the engine at idle and in reverse, and spend the next three hours working on it. Eventually, we gave up, hitchhiked to the ferry landing, and went home.

Ruined Moment of Triumph facts LibreShot

47. Redlight

We had a terrible coworker. He was fired after being written up for being tardy three times in 30 days. I was out with the boss in the parking lot on lunch while HR went through the termination process with him. When he walked out, he saw us standing there, jumped into his convertible, pulled up to where we stood, flipped off the boss screaming some choice words, then floored it toward the exit of the lot.

The exit was only about 10 feet away and was blocked by traffic waiting on a red light. So, we stood there and laughed at him for a good 30 seconds while he waited for the light to change and traffic to get out of the way. He didn't say anything. He must have been so mad and embarrassed.

Ruined Moment of Triumph facts Flickr, Chris Phan

48. Long Time No See

My ex had moved back into our small town after breaking up with her new boyfriend (my ex-roommate). I never avoided her, but I was lucky enough to not lay eyes on her for over a year when I heard she was moving again. That day, as she was walking to her car for the last time to pull out of town, we locked eyes as I came out of a coffee shop.

Holding her gaze, I take one step towards her, inexplicably failing to notice the signboard on the sidewalk, right in front of me. Coffee flies. I fly. From my newly acquired position of moral authority—half on the sidewalk, half in the gutter—I firmly, calmly, say, “Hello. Heard you were in town.” She replies, “You're lying in dog poo” and rides off into the sunset.

Embarrassing Moments factsShutterstock

49. Drive-thru Drive-by

I worked at McDonald's when I was in high school and finally got a better job, with better hours, closer to home after a couple of years there. When I quit, I was annoyed to learn that they wanted my greasy threadbare uniform polo and pants back after I was done. See, I didn't want them, but it seemed cheap and sort of insulting—they were just going to throw them away, same as I would, but they were going to require an extra trip back there for me to do it? No, I don't think so. Screw them.

Keep in mind I was 16 at the time, and apply "I'm such a rebellious free thinker" teenage arrogance to the situation. What happened next makes more sense that way. So, on my last day, I went out to my car, stripped down to my boxers, went through the drive-thru, and threw my wadded-up uniform at the woman working the window.

That's when told her to give them to the owner. The look on her face was priceless. I drove off, music blaring, feeling ridiculously happy and proud of what I had just done, and happened to run into a friend of mine who was also cruising around. I explained why I wasn't wearing a shirt or pants, he laughed and said we should go get something to eat.

Sure, no problem, I'll just change into the clothes I brought, grab my wallet, and...Ah, crud. That’s right. My wallet was still in the pocket of the pants I'd thrown in the drive-thru window. I had to slink back in, sheepishly ask someone to search through the trash for me to find my pants and find my wallet. They did.

I didn't go back to that McDonald's for years.

Drive-Thru Customer Experiences factsShutterstock

 

Sources: Reddit,


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