35 Times People Challenged An Expert And Were Given A Reality Check

Ever watched someone confidently step up to the plate only to get totally outclassed by an expert?

It’s a pretty satisfying sight, and the internet has tons of hilarious stories where amateurs underestimated the people they were challenging.

In a recent thread on Reddit, people are sharing the times they didn’t just defend their skills—they showcased them in unforgettable ways, whether it’s a Christmas wrapping competition, chess showdown, or trivia face-off.

These are tales of quiet (and sometimes not-so-quiet) victories, where a little know-how met a lot of attitude.

Keep going for moments where people who “knew better” quickly found out they didn’t.

1.

a pile of christmas wrapping paper on top of each other
Photo by Cody Chan on Unsplash

I have been wrapping my family’s Christmas presents since a very young age. It’s the perfect activity to focus my crippling perfectionism with my overall anxiety riddled self to create a beautiful masterpiece that would make anyone think twice about discovering the mysteries beneath the colorful paper and bows. I have just always loved to do it and my mom was more than happy to not spend hours wrapping presents.

Flash forward to the company Christmas party in my late 20s. We are split into teams to compete for random prizes, I am up for the next game. I had no idea what I would be doing. I see a big cardboard box, a neck tie, wrapping paper, scissors, tape and a bow….I know what’s about to go down and I am here for it!

It’s a blind present wrapping challenge.

My competitors start talking about how they can wrap presents fast and I sit there silently staring down that cardboard box knowing fully that the crowd is in for a show.

Blindfolds (neckties) go on, we have a partner that isn’t blindfolded that is supposed to give verbal directions. Just before the timer starts, I lean over to my partner and say quietly “are you ready for this?” And she just say “what?!” Bam, timer starts, partner tries to give directions at first and quickly realizes I’m way ahead of her. Before anyone else can even get their paper cut, I’ve got my box wrapped, taped, and bowed. I even folded the ends in ‘fancy’ to have the triangles meet. And that, my friends, is how I earned the most satisfying $10 Starbucks gift card of my life and earned the title of wrap-master.

2.

Colour. It sounds weird but anytime the colour of something comes up and someone tries to correct me.

I’ve been a commercial printing press operator for 20 years. I can spot VERY subtle differences in colours that most people can’t.

Edit: The upvote is orange. The dress is blue and black.

3.

I’m going to date myself here but I was in undergrad when the video game Halo was released. I never really played video games, but at the time I had a boyfriend (I am a girl) who was really into it. We played. A lot. Even went to some college based tournament games and did well.

Fast forward some years later and my husband and I are at a house party. Someone turns on the Xbox and was looking for a 4th for Halo. My husband volunteers me. The guys were visibly not thrilled but played along. I wiped the floor with them. Eventually they decided to team up 3 against me. Still destroyed them. The whole party ended up crowding around us to watch. It was a great night. 🙂

4.

Kinda the reverse, for me. I’m a physical education teacher and I had a student that took a pretty bad tumble in class. Hit her head on the wall. Pretty clear concussion symptoms. So we get her stable, call mom & dad to come get her.

Dad shows up & I start going through the concussion symptoms and treatments with him. Letting him know that a doctors visit is probably in order. Blah blah blah I keep going on and on about concussions. He just politely nods and thanks me.

He takes daughter and leaves, and I see my principal standing behind me and he can barely contain his laughter. Turns out dad is an emergency room doctor. And he just sat there while his daughter’s gym teacher gave him medical advice.

5.

Engineer with Map in Grassfield
Photo by TUBARONES PHOTOGRAPHY on Pexels

Female mechanical engineer. My life is pretty much people challenging me on things I’m an expert on.

6.

I have perfect pitch.

It’s not a thing I can turn off, notes simply ARE a pitch clear as day, much like how red is clearly distinct from green.

Anywho, music class in junior high. Teacher explains that Mozart had perfect pitch and walks over to the piano, plays a note and says “and just by hearing it, he’d be able to tell you what now that was… now can any of YOU do that?”

At the time, I honestly had no idea this was rare. Raise hand, teacher with a smug look points and me and is gobsmacked when I answer correctly with note and octave. Figures it’s pure luck so does it again and asks me to face the other way. I answer correctly again.

Tries it with chords, sequences and two hands worth of notes. Still right every time. Ends with me playing back a short sequence after listening to it blind.

That day, I learned that perfect pitch is actually kind of rare.

7.

While I was in high school I was the reigning city fencing champion, in both the youth and adult tournaments. My high school decided to do a school-wide fencing unit for Phys. Ed. and the coach they brought in to teach all of the students was my actual coach. During my classes, my coach naturally brought me up to help demonstrate the various moves, but for some reason one of my classmates didn’t understand that I wasn’t chosen at random. He started talking s**t about how I looked like I didn’t know what I was doing, and how he could probably kick my a*s in a duel. Now, he actually was pretty good for a guy who’d never fenced before, and at the first opportunity to actually have a bout, he decided to have a go at me.

I picked him apart and did not give up a single touch, and used the opportunity to practice my parry and ripostes (I admit, I took a bit of sadistic pleasure in thoroughly beating him).

Afterwards, my coach made a point of congratulating the other guy for doing so well against the city champ, which changed his attitude considerably.

8.

I have a PhD in genetics, and I’ve published multiple papers on viral vectors spreading in large populations.

Every f*****g anti-Vaxer and COVID conspiracy theorist. I’m so sick of it.

Also, when someone I met at a social event found out that I work in a genetics research lab, he asked the following question:

“If two white Americans go to China and have a baby there, will it come out Asian?”

I was so shocked that I actually spit out my drink.

9.

The property management company for my homeowner’s association insisted that I had received emails that I never received. So I asked them to prove that I had received them. They said they’re sure I received them.

I’m a software engineer and at the time I had just finished an enterprise email delivery system (like an in-house Constant Contact). I knew the rules of the CAN-SPAM Act by heart. I KNEW exactly how their system worked.

So this real b***h of a property manager said “I know how email works. You wouldn’t understand.” I mentally did the arrogant knuckle crack and started to explain – very methodically – how email delivery works and how they’d track various actions. I spent about five minutes detailing my credentials and why I was absolutely certain they had never sent me the emails they alleged I received. When I was finished, the HOA board just agreed to waive the fines.

10.

A Woman Playing a Video Game
Photo by ROMAN ODINTSOV on Pexels

I used to play fighting games competitively all over the world. Never made one of the top slots but I could usually hold my own. One of my best game was Super Street Fighter 2.

Went to a bar by work one day and they just so happened to have an SNES set up with SF2. I order a drink, pick random characters and just f**k around for a bit. Some guy comes in and immediately starts bragging to his date that he’s the best SF2 player ever. I asked him to play some games against me and offered to buy him a drink if he could beat 2 out of 3. Twelve games later I am completed hammered and he finally gives up and leaves. Still don’t remember getting home that night.

11.

Trivia. I know all sorts of weird random facts.

One day a co-worker said, “If you’re so smart, why don’t you come down to the Legion’s trivia night?”

I am no longer welcome at the Legion’s trivia night because of how badly I beat everyone.

12.

By no means an expert (I’d probably rate in the 1500s), but I’ve played chess since I was a small child and was the best player in the middle school chess club. The guy who owned the pool hall me and my juvenile delinquent friends hung out in was talking about how dumb kids are these days and said he bet nobody in my group of hoodlums could play chess. I beat him soundly, then again in the rematch.

13.

Not me but my friend used to ride a unicycle as a kid. He worked construction and they were working at a house that had an old unicycle.

The other workers tried riding it and immediately fell off. My friend walked over to it and inspected the unicycle like it was the first time he ever saw one then said it didn’t look that difficult. They all laughed at him and he said he thought he could ride it. Eventually one of them bet him $100 he couldn’t ride it. He jumped on it and immediately rode down the street.

14.

Not quite this but I tried to learn piano years ago, I bought a keyboard and learned the first movement of moonlight sonata but it was literally all I could play.

I had just started a new job as a chef in a fancy hotel, had been there maybe a month and was at the Christmas party, I sat at a piano and the head chef pointed me out, laughing and said “look at splifflizard, you cant play the piano”, I thought I’ll just act confident and play the only thing I can so was like “yeah i can.. I’ve played for years” and he said “oh really? Play moonlight sonata then”, couldn’t have gone better. He was gobsmacked and I never told anyone there that I was actually c**p at piano except that one song lol.

15.

A Woman Holding a Fencing Sword
Photo by cottonbro studio on Pexels

Medieval Faire, 2002. Carnie running the fencing game picks me out of the crowd for being tall, and challenges me to a free bout against “The Master”. Not a lot of people fence, so his gambit probably worked most of the time, but when he handed me that saber, I handed him his a*s.

16.

Not an expert but after having to deal with a chemistry teacher in middle school who basically hated me for no reason, I had to put extra effort in the class so I was really good in that class.

So this one time in high school a mean girl hid my test. I got called to the principal’s office to inform me they couldn’t find my answer sheet even though lists showed I attended class that day. Anyway, I went to the TI office, searched my answer sheet through all the groups (I’m talking a class of 500+ people).

Since my exam wasn’t found the person in charge of the department started bitching at me that I did it on purpose because probably I knew I was failing, and I told her, “well give another test, I’ll do it,” and she thought that was a big red flag because probably I just memorized all the answers blah blah. I told her, “just give a bunch of exercises, and I’ll solve it right here right now, I bet my entire grade on this, do you really think I planned to spend all the week looking for that test.”

So she goes and gives me 10 exercises. I scored 10/10.

**In. Your. F*****g. Face.**

Safe to say I don’t know s**t about chemistry anymore lol.

PSA: I found out what happened to my test because the girl was bragging about taking my test and throwing it to the garbage later that year.

17.

I wouldn’t say I’m an expert at push ups but I’ve worked in the fitness industry for 20 years and workout myself fairly regularly. Doing 20 push ups isn’t anything to me. I was at a party that was attended primarily by what I would call hipsters. A guy (who had been drinking a fair amount) challenged me to 20 push ups as fast as possible for $20. I won and got $20. Then another said he would do the same bet if we went right away (I guess thinking I was kinda tired). I beat him and got another $20. A few minutes later another guy did the same bet. It was an easy $60.

18.

This happens to me a lot. I had the unique situation of working in manufacturing in China for 7 years. I moved back 3 years ago and constantly have people explain to me why manufacturing could easily come back to the states. I emphatically tell them they are f*****g high.

19.

As someone with a history degree – basically everyone thinks they know it better than you. It’s endless.

History repeats itself, and those who study it are doomed to helplessly watch it repeat itself.

20.

Selective Focus Photography of Assorted-brand Liquor Bottles
Photo by EVG Kowalievska on Pexels

Someone once tried to insist that our state didn’t sell alcohol on Sundays.

I’ve spent over a decade working in restaurants and am also an alcoholic, which she knew about but still insisted on arguing with me about it.

21.

Well I am a veterinarian and I know how to prevent fleas.

(Them) “My dog is itching and it’s not fleas”

(Me) “Ok but your dog is infested”

(Them) “…it’s not fleas”

..run comb and show them hundreds…

22.

I’m an academy award winning sound mixer and almost everyone on film sets think they know my job better than me.

23.

Pool water treatment isn’t very difficult even for the average joe. Trust me, you do not need to pay someone $100 a month to treat and clean your pool. I love to listen to the sales people at Leslie’s (local chain of pool supply stores) “educate” me and their other customers. I got into a polite discussion about algae one time and I was told that I was wrong. I explained that I knew what I was talking about. He asked what I did and I responded “industrial water treatment.” He’s very nice to me when I go into the store now.

24.

When we were having a couple drinks on Friday after work, I was challenged to a shooting, by a colleague. Little did he know I’ve been shooting air rifles competitively ever since I was thirteen. Not to say I am the greatest, but I’ve made it to the national finals for my country multiple times, and came third and sixth. I have all the special clothes and gear and such you need to make it to such a level.

The next day, Saturday, we showed up to the range I always shoot at. It’s not a day I usually train, so not many people recognize me. I beat his a*s left, right, and center that day. Out of 600 points, he scored about 200-250 if I remember correctly. I got about 580, which was about average of what I used to shoot.

He had to buy me a fancy bottle of whisky and now we shoot every two or three weeks together. Fun times.

25.

Abstract textured surface of picture made of brown paint on white sheet
Photo by Photo By: Kaboompics.com on Pexels

A friend of mine challenged me when I said the dusty bits on the floor below their air conditioner was because they needed to clean the filter. They insisted that it was ash coming from outside through the air conditioner because of fires that had been going on nearby. It was a split system AC, I work in HVAC. At least once I explained how their unit worked, they conceded.

26.

A beginning writer asked some advice about a basic drafting method, so I offered my point of view. Some tough guy decided to butt in and say that what I said was proof I’m not a “real writer” and it was obvious I would never be published. At that time, the second or third book in my trilogy was about to be released. I asked the guy not to tell my editor that I wasn’t a real writer.

27.

Krull. The arcade video game. A guy tried to hit on me at a house party by challenging me to a game, but he knew he had made a mistake when I said, “Sure, I haven’t played in a while.”

It was my boyfriend’s house, and his game.

We still had fun playing though.

28.

Guitar Hero. Work held a Christmas party at a venue and set up the game for fun and prizes. I was the second oldest (47f) person there. All the younger employees were going ham and having a great time. I wasn’t going to play until the prize was $500 for last person standing. I walked away $500 richer and also a legend.

29.

I’m no expert but people never assume I can play Pool. I grew up with my parents going to the pub, so as an early teen would play A LOT of Pool and got pretty good.

There’s been a number of occasions where I’ve got us a round of drinks or stuck it to some knob who’s hogging the table.

30.

red and black human face
Photo by Joshua Fuller on Unsplash

My roommate who took a psych 101 class at a prestigious university told me, a master’s level therapist, that the movie Split (with James Mcavoy) was an accurate depiction of “multi-personality disorder.”

31.

Went to a couples night once and the guy had wall to wall movies and framed posters in his basement, super into it. Mentioned I used to be a movie nerd but not so much anymore. He challenged us to a movie trivia board game, kinda in a condescending way, and I tried to politely decline but my gf insisted we play. They went first, missed the question, then we ran the table. Never heard from them again.

32.

Hula hooping: They resorted to throwing stuff at my hoop, because I kept going like the Energizer Bunny.

33.

A former coworker challenged me to a cheese eating competition at an office get together. Little did he know I f*****g love cheese and am the type of person to eat shredded cheese straight out the bag at 3am. He wimped out after 15 cubes of cheese from the deli platter while I basically cleared my whole section.

34.

I hesitate to say “expert” but compared to this person I was a savant. I did a few papers throughout school on GMOs for some presentations so while I am not an “expert” I know more than a random Joe, especially at the time.

Well I remember getting into an argument with a stereotypical college hipster about how “unnatural” GMOs were and how we should stop using them. Just your usual buzzwords “chemicals are bad” and the like.

Being able to systematically shut her down until it became “I don’t *feel* like they are safe.” Was pretty nice though. And for the record I don’t generally revel in this sort of thing, but if you could hear the tone she used….I think you’d understand.

35.

a man holding three cds in front of his face
Photo by Kreative Kwame on Unsplash

My father in law challenged me about the capabilities of DVD. Specifically he claimed that you could only have widescreen video (not 4:3) on a DVD disc.

At the time I was employed as a DVD author. I authored the very first commercially available feature on Scenarist. I am literally acknowledged in the first edition of “DVD Demystified” as an expert. I had already by that time personally authored literally hundreds of DVDs with 4:3 video.

He knew all of the above at the time, yet still insisted I was wrong.

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Alex Buscemi

Alex Buscemi

Writer. Billionaire. Astronaut. Compulsive liar.

@whatsupboosh on socials.