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16 Cringeworthy Things People Say to Impress Someone, Do You Too?

When we’re trying to impress someone, we can sometimes say things that we later regret. Whether it’s a compliment that goes awry or a joke that falls flat, we’ve all been there.

A netizen recently asked, What is the most embarrassing thing you’ve ever said to someone you were trying to impress? The responses below shall have you rolling!

I asked Tom Morello If He Knew Who He Was

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“I worked at the local guitar shop in town in high school. It happens to be Tom Morello’s hometown (of rage against the machine fame).  The owner used to babysit him when Tom was little and he’d always stop by to say hi when they were in town on tour.

This was around the time of Evil Empire and they were at peak popularity.  He came in one day while I was there and asked if John was in. 16-year-old me just looked at him and asked “Do you know who you are?!?!” He just laughed and said yes.  Humiliated, I went and got the owner and then tried to hide and die from shame.” 

I Accidentally Reminded My Cousin Of Their First Wedding On The Day They Were Getting Remarried 

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“I was around 15, going through the receiving line at my cousin’s wedding. This was my first “grown-up” wedding and I wanted to act it. As I hugged my cousin I blurted out “I’m so excited to be here! The last wedding I was at was your first one!”

That has echoed in my head for 30 years. BTW, this was my cousin’s second wedding. The groom’s first.” 

Messed Up The Ice Cream Name Badly In Front Of A Crush

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“Crush in HS worked at an ice cream store. When she asked for toppings I said “I’ll have Reese’s peennises please”. The store laughed.” 

I Told Everyone I Knew That I Was Going To Cross The Atlantic To Hire A Prostitute 

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“I told everyone I knew about my plan to go on a trip to Europe. I had planned to tour different countries by train with a special visit to… Amsterdam.

My intention was to visit a marijuana cafe, but in my ignorance, I thought that these were all located in the red lights district. I would tell people I was going to the red light district and they would understandably pause and ask me… why? Trying to be sly, I would say something like “to do what the locals do of course,” believing that this meant smoking marijuana in a cafe…

I was actually telling everyone I knew, friends, teachers, relatives, coworkers, that I was going to cross the Atlantic so I could hire a prostitute…”

Told A Music Band That Their Show Was Great When They Didn’t Even Play That Day

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“Went to Warped Tour, they had a contest to submit a photo and the winner got to meet one of the bands.

Took a sick shot with my Blackberry, submitted it in its low-resolution glory and won somehow. Honestly, I had no idea who the band was, but I met them, got a signed poster, and shook all their hands. 

Then I said, “You guys were awesome, great show”.

Singer said “Well, we haven’t played yet so…”.”

I Said I Can Do A Kickflip & Ended Up Snapping My Ankle

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“I can do a Kickflip, then proceed to elegantly snap my ankle.” Said one. 

“Reminds me of my friend at a party trying to impress girls doing a kickflip with a longboard and proceeded  to break it in two.” Another added.

Almost Fat-Shamed A Lady At The Restaurant 

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“Server trying to get a tip: I went to clear a shared dessert dish from a table of 4 – mom, dad and 2 sons.  One son jokingly pointed at his mom and said “She ate most of it”. I, a braindead server who was/is terrible at banter, but trying to get a tip said the first reply that came to mind:  “I can tell”      

No idea why. Terrible reaction, as expected.  No tip.”

Told A Girl I Didn’t Know The Capital Of Austria While Wearing A T-shirt With “Vienna” On It

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“I did once (truthfully) tell a girl from Austria that I didn’t know what the capital of Austria was – which wouldn’t be too embarrassing, except that I was wearing a t-shirt which said ‘Vienna Rocks” on it at the time. She thought I was joking.”

Told A Musician I Liked A Song (It Wasn’t His)

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“I told a musician I like that I liked a specific song. It was not his song.” 

I Reached My Hand Onto A Guy’s Thigh Thinking It Was My Girlfriend 

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“I was on an airplane years ago with my girlfriend and her parents. My girlfriend couldn’t get a seat next to me and sat directly behind me.

During the flight, I thought I would surprise her and reached my hand back onto her knee. Slowly I kept extending it up her thigh until I heard giggling.

Looked behind the seats and saw that my hand was on the leg of the guy next to her. He saw my face and said, “I just wanted to see how far you’d go.” Of course, my girlfriend was in on it and started laughing along with the rest of the row. Was so embarrassed.”

Told A Girl Her Mother Sounds Like A Dinosaur 

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“When I was a kid at tennis camp, I was sitting next to the new girl when I heard this weird scream from the upper tennis court. I tried to make her laugh by saying “That sounds like a dinosaur”. All she said back was “That’s my mother”.”

I Set Fire To The Restaurant, And Later Spilled The Drink On Someone 

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“Not an embarrassing thing to say but when I was first dating my now wife I set fire to the restaurant, and some random guy at the table next to me put it out. So I bought him a drink to say thanks and spilled it on his date. 

Wanted to die.

Told My Crush I Broke The Foosball Table

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“Was wrestling with a friend and we fell on and broke a Foosball table. My crush walked into the room and I said with a stupid smile, “I did that crap.” She left without a word.”

Told My Then Partner That Her Eyes Were Like Mushrooms 

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“Your eyes are like Mushrooms. She laughed so hard that we dated for 7 years.” Said one.

“If it is stupid but it works, it isn’t stupid.” Another added.

My Dad Told A Latin Teacher That He Was Studying Latin Even Though All He Knew Was A Single Word

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“When my dad was a kid, he tried to impress an older lady. She had asked him what he was studying, and he confidently told her “Latin”. She seemed really impressed by this, so she asked him to speak a bit of Latin to her. He knew one word and created a bunch of other words around it that sounded Latin-ish. She frowned and told him it was a bad thing to lie.

Her job? Latin teacher.”

I described Myself As “Lazy” At A Job Interview 

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“Not trying to date someone, but at my first job interview, I got a question that was: ‘Describe yourself in 3 words.’ I literally said ‘lazy’. Somehow I still got the job.”

Tried To Tell My Boss Who Had Just Broke His Arm That “His Arm Was Broken”

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“One day I went to my boss’s chamber and saw his arm in a cast. I wanted to say something sympathetic and score some brownie points but what I said was “Sir, your arm is broken”. He looked at me and said “I know”.”

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The article was originally published on Mrs Daaku Studio.