20 Times Someone Blurted Out Something Embarrassing To Someone They Were Trying To Impress

Published 1 year ago

If you’ve ever opened your mouth and spouted something totally embarrassing you are not alone. We all have such episodes at least once in our lives and today we explore a very honest discussion on Reddit that delves further into the subject. 

In fact, the conversation took a very entertaining turn after one user asked folks to spill the tea about the most embarrassing things they’ve ever said to someone they were actually trying really hard to impress. As usual, folks delivered with enthralling tales and we’ve shared the best of the best below. 

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Image source: skam_skins, Katie Salerno

Kissed a girl for the first time when I was 13, something prompted me to say “average” and she loathed me for the rest of the academic year. Cut to 6 years later I matched with her on bumble. We met, we sexed and she looked me dead in the eye and said “average”. She is my bestfriend now.


Image source: BIRDsnoozer, Alexander Krivitskiy

Went to catholic school.

Lots of Ukrainian classmates.

Had a crush on a Ukrainian girl, so I asked some Ukrainian friends what I could say to her. A pickup line maybe.

So at lunch I went to her and said (and I’m probably not spelling any of these correctly) “Di me ni hlib tper!” She laughed so I went back to my friends and asked for another.

“Ya ye dournee” she laughed a bit harder. This was good material. I went back and asked for another.

“Ya popishya moi shtaneh” she spit pop and was in hysterics.

The first was, “Give me a piece of bread!”

The second was, “I’m stupud!”

And the last was, “I pissed my pants!”

Those a******s got me a couple dates with her tho!


Image source: matthewmichael, ROMAN ODINTSOV

I worked at the local guitar shop in town in highschool. It happens to be tom Morello’s home town (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.


Image source: HunterIceFool, Ron Lach

“Hey everyone, check this out!”
Trying to attract the attention of a beautiful girl who sang soprano in the choral program at music camp. I was a gangly violinist. We were tossing a Frisbee around.

I’d been practicing the classic, “under-the-leg” Frisbee throw. It was time to reveal my move.
A dozen campers, including my crush, looked directly at me.
I lifted my leg, flung the bee, caught it on my right pinky. It shot like a flying blade of plastic sideways and proceeded to hit my crush directly in the THROAT.
She collapsed, gasping.
She couldn’t sing for the rest of the camp season.

This is the last memory I will experience as the wave of DMT floods my brain with the soft light of death.


Image source: WhaleyWino235, Maria Orlova

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


Image source: Murphyitsnotyou

Was sat round a camp fire at a festival with a few friends and some random women that had joined us. Everyone was drinking, talking and having a good time.

One of the women got up and said to her friends “I’m gonna go and grab something from the tent, you coming?”.

One friend replied “nah, I’m gonna stay here and get f****d”.

My drunken stupid a**e took it wrong and blurted out “I’ll f**k ya”.

She looks a bit shocked and goes “that’s not really what I meant but thanks I guess”.

She meant get f****d up on booze and I still cringe about it almost 30 years later.


Image source: owlfigurine, Bruno Bueno

Not me but my husband. For context we’ve known each other since kindergarten and started dating at 14.

I was in a very edgy emo phase at 14 (it was 2007, weren’t we all) and my husband, trying to impress me, and thinking I was into the “bad boy” type lied and told me that he had gone to jail over the summer. I knew this was not true, again we’d known each other since kindergarten and he was the most well behaved and easy-going kid I knew, so I asked him why he went to jail. What his 14 year old brain came up with as a cool but not too serious reason to be in jail was that he “got too high and threw a Twinkie at an old woman while he was skateboarding, but it hit her too hard, and she fell and got knocked unconscious”

I remember him saying this with 100% sincerity as I sat there trying my hardest not to crack up because I had a crush on him and he was a big dork, but it was charming. I could see that he instantly regretted saying that, like I could visibly see it on his face as he realized how stupid that sounded but I dropped it at the time and didn’t bring it back up again until years later when we were more comfortable with each other. We’re 30 now and I still bring it up as a joke on occasion, our kids now also think it’s hilarious.


Image source: inexistences, Marcus Aurelius

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.


Image source: PancakesandScotch, ima Miroshnichenko

First girlfriend, 6th grade, went to the movies.

Wanted to hold her hand, terrified, wasn’t sure what to do. Started giving her a sales pitch on how awesome my hands were.

“They’re really good at holding stuff, like boxes…or jugs”

Was truly thinking of milk jugs (god knows why) but accidentally suggested I could just hold her boobs.

It’s been more than 20 years and I still think of it regularly


Image source: PhoenixSidePeen, cottonbro studio

I had a crush on the receptionist of my college’s gym. One night when I was the last one in there, I got nervous making small talk and offered to help her clean up before she closed the gym, and I immediately thought to myself “wow you sound like a f*****g serial killer”

She actually got the vacuum out for me and proceeded to talk about her boyfriend. At the end of the day, not mad since I did something nice for someone lol


Image source: DaPanda21919, Alex Green

Not trying to date someone, but my first job interview, i got a question that was: ‘describe yourself in 3 words.’ My a*s literally said ‘lazy’. Somehow still got the job


Image source: DM_ME_CHARMANDERS, Volkan Vardar

Not embarrassing thing said 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.

EDIT: woah. I went on the p**s and came back to my wife WhatsApping me

Hi babe.


Image source: Ladon1949, Athena

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 me hand back onto her knee. Slowly I kept extending it up her thigh until I heard giggling. Looked behind through 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


Image source: SuvenPan, Ben Sutherland

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”.


Image source: Virtual-Elderberry31, Chait Goli

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 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…


Image source: NoFroggie, Helena Lopes

Not me, my husband.
In the beginning of our relationship he was soo bad at complimenting but he felt the need to do it anyway.

So once when we traveled by bus together he just kept staring at me with loving eyes and said
‘You are so different than anyone I ever meet… you… you.. i think… you degenerate from society.’

I said ‘Oh, wow! NOW I feel so special.’

His face went white and started to stutter but I laughed it off.

Some times later we were at a bus stop full of people and he blurted out loud.

‘Your hair is so pretty! How did you do it? Like did you wash it or what?’

‘Yeah, I never do that before but I like to shake things up sometimes.’

He got a cold and a running nose, but he never had any handkerchief at hand. I thought out some romantic gesture (i was 17 at the time) I brought some tissue paper with me, but on one, I write a loving note to him.
He saw the note… Read the note… and blew his nose in it. -.-

I gave up on romantic then.
He is my husband, best friend for many years now and the father of my children. ??


Image source: Wisdom_of_the_ages, Kasumi Loffler

It wasn’t me, but a very loud phone conversation that was almost impossible not to listen in on the LRT ride home. A guy is trying to impress a woman on the other line by acting tough, saying if some other guy does anything out of line, he’ll “bruschetta him really good”.

Like, you’ll invite him over for appetizers?

You can tell the woman isn’t getting it either because he keeps on trying to explain it to her, and he’s getting more and more agitated. He has a bruschetta at home, he’s ready to go at any time.

Finally it gets to the point that he realizes she doesn’t know what he means by bruschetta and he explains it’s a knife that they use to cut through underbrush in the rainforest.

He means machete.

At this point I lose it laughing and dude looked like he was both ready to throw down and was dying a little inside.

It’s been probably 12 years and I still think about this often.


Image source: mymindisanenigma420, Kara Adora

When I started dating this guy I met at Warped Tour the summer before starting college, his dad wanted to meet me because apparently it was a red flag for his son to have met a girl at a concert. I went over to his house to meet his father and when he asked what I would be majoring in I said “I will be majoring in minoring”… I turned bright red and tried to correct myself. A few minutes in and his dad busted up laughing. He thankfully instantly liked me after that and now here I am 13 years later married to the guy I met at Warped Tour.


Image source: Ok-Fudge8848, Katerina Holmes

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.


Image source: Sonnyboy1990, Keira Burton

Trying to lie about my age.

Her: _”You’re too young, how old are you?”_

Me: _”I..eh um..I’m like 20 or 21 I am.”_

As the Sentence left my mouth I realised how ridiculous I had just sounded.

**For clarification, I was 17 and absolutely hammered at the time.**

Shanilou Perera

Shanilou has always loved reading and learning about the world we live in. While she enjoys fictional books and stories just as much, since childhood she was especially fascinated by encyclopaedias and strangely enough, self-help books. As a kid, she spent most of her time consuming as much knowledge as she could get her hands on and could always be found at the library. Now, she still enjoys finding out about all the amazing things that surround us in our day-to-day lives and is blessed to be able to write about them to share with the whole world as a profession.

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