The most cringeworthy moment in your life

[Talk Talk]

This might have been done before.

My personal maximum embarrassment was when I was about 18 and used to travel to work on a company coach. There was a particular sweet young lady who worked in Personnel (as it was called in those days), who I used to sit next to occasionally.  Her name was Karen Wood and she was one of the nicest, softest caring type of person who I have ever met. Unfortunately athough lovely, she had a dental condition that an orthodontist would have paid to rectify. She was goofy. It was in December when this happened.

The conversation went something like.

Alan: "Hello Karen. How are you?"
Karen: "Yes, very well thank you. I'm glad we have the holiday coming up."
Alan: "Too right, I can't wait for the break."
Karen: " Will you be staying around for Christmas?"
Alan: "Yes, with my parents as usual."
Karen: "That's nice, I hope you have a good time with them."
Alan: "It is usually pretty good."
Karen: "Do you think you will get any nice presents?"
Alan (singing): "All I want for Christmas is my two front teeth."

ugh

ick

aaaargh

Truly stupid, horrible and inconsiderate. I still hate myself.

[Doore]

I might have had a beer or two, but that's fucking brilliant I reckon.

[Doore]

Oh, and my contribution, using a line I'd heard on Men Behaving Badly.

At the bar in a club in Cardiff:

BS: Hi, my name's Billy, can I stand here?
Pretty lady: No
BS: Oh, OK then.

I went to the other end of the bar to order my solitary drink in shame.

[Bogus Dave]

I asked a man in morrisons if he needed a hand getting something off the shelf, as he was struggling.

Only when he turned to face me did i realise he only had one arm...

[leefer]

When i was about thirteen i got this amazing crush on a girl in my class,it got so bad every morning early on my paper round i picked a flower from her front garden..tulips and daffs were taken untill one morning a red faced old man came out in a rage..what the fuk you doing he screamed as i was tugging on a wallflower or something similar ..it was the first time i had heard an old person swear...anyway i found the courage to tell him that i was in love with his daughter...bloody hell he said shes thirty five and got kids!
Turned out i was given duff imformation on ware she lived.

[Mexicano Rojo]

My exs mum walked in on me hanging out the back of her daughter.

[leefer]

I asked a man in morrisons if he needed a hand getting something off the shelf, as he was struggling.

Only when he turned to face me did i realise he only had one arm...

I suppose he would have been better off in a seconhand shop.

[Nemo]

I suppose he would have been better off in a seconhand shop.

Fuck off Neville...

oh.

[Saxondale]

I asked a man in morrisons if he needed a hand getting something off the shelf, as he was struggling.

Only when he turned to face me did i realise he only had one arm...

Did the same with dizzee rascals dj semtex who also only has one hands.  Something I didnt realise when I asked if he needed a hand with his record bag.  'Do you want a hand' sometimes sounds bad.

[4D]

This might have been done before.

My personal maximum embarrassment was when I was about 18 and used to travel to work on a company coach. There was a particular sweet young lady who worked in Personnel (as it was called in those days), who I used to sit next to occasionally.  Her name was Karen Wood and she was one of the nicest, softest caring type of person who I have ever met. Unfortunately athough lovely, she had a dental condition that an orthodontist would have paid to rectify. She was goofy. It was in December when this happened.

The conversation went something like.

Alan: "Hello Karen. How are you?"
Karen: "Yes, very well thank you. I'm glad we have the holiday coming up."
Alan: "Too right, I can't wait for the break."
Karen: " Will you be staying around for Christmas?"
Alan: "Yes, with my parents as usual."
Karen: "That's nice, I hope you have a good time with them."
Alan: "It is usually pretty good."
Karen: "Do you think you will get any nice presents?"
Alan (singing): "All I want for Christmas is my two front teeth."

ugh

ick

aaaargh

Truly stupid, horrible and inconsiderate. I still hate myself.

Surprised you didn't lose yours 

[nevillew]

Fuck off Neville...

oh.

  Nice one leefer.

[dell boy]

At the age of 16 I was working in a bindery as part of my training in print. I was the only bloke working alongside 20 or so mature women, sex and the size of the mans privates seemed to be the normal talk of the day. They were bloody intimidating and would try to have a feel at what was in trousers at any chance during work and you had to be on your guard at all times. This might seem to youngsters of today as a good opportunity to experience your sexual desires, but I can tell you these women were frightening and once they had something on you, well you were dead.
On the third morning I worked in the department, I went for a piss and carelessly caught by willie in my zip, well and truly caught. After crying with pain for about 5 minutes I had no other option but to ask for assistance from one of my work colleagues. One meant 20 came to assist and most took great joy in taking turns in trying to free by willie.
If you've ever worked on a production line full of women you can imagine what they tried to do to me. They finally cut away the zip and left me sitting in my underpants for 30 minutes whilst they mended by trousers.

[Arriba]

did you sample any of them though dell?

[Matchworn Shirts]

At the age of 16 I was working in a bindery as part of my training in print. I was the only bloke working alongside 20 or so mature women, sex and the size of the mans privates seemed to be the normal talk of the day. They were bloody intimidating and would try to have a feel at what was in trousers at any chance during work and you had to be on your guard at all times. This might seem to youngsters of today as a good opportunity to experience your sexual desires, but I can tell you these women were frightening and once they had something on you, well you were dead.
On the third morning I worked in the department, I went for a piss and carelessly caught by willie in my zip, well and truly caught. After crying with pain for about 5 minutes I had no other option but to ask for assistance from one of my work colleagues. One meant 20 came to assist and most took great joy in taking turns in trying to free by willie.
If you've ever worked on a production line full of women you can imagine what they tried to do to me. They finally cut away the zip and left me sitting in my underpants for 30 minutes whilst they mended by trousers.

Bloody hell, Ben Stiller posts on thetownend

[Nomoreheroes]

This might have been done before.

My personal maximum embarrassment was when I was about 18 and used to travel to work on a company coach. There was a particular sweet young lady who worked in Personnel (as it was called in those days), who I used to sit next to occasionally.  Her name was Karen Wood and she was one of the nicest, softest caring type of person who I have ever met. Unfortunately athough lovely, she had a dental condition that an orthodontist would have paid to rectify. She was goofy. It was in December when this happened.

The conversation went something like.

Alan: "Hello Karen. How are you?"
Karen: "Yes, very well thank you. I'm glad we have the holiday coming up."
Alan: "Too right, I can't wait for the break."
Karen: " Will you be staying around for Christmas?"
Alan: "Yes, with my parents as usual."
Karen: "That's nice, I hope you have a good time with them."
Alan: "It is usually pretty good."
Karen: "Do you think you will get any nice presents?"
Alan (singing): "All I want for Christmas is my two front teeth."

ugh

ick

aaaargh

Truly stupid, horrible and inconsiderate. I still hate myself.

I can't get this out of my head! I've got to ask - What did poor Karen do? Did the smile disappear from her face and a little tear come to her eye? Did she look at you with daggers in her eyes, huff and look away? Did you apologise? Did you ever talk to her again? What is she doing now? Is she mentally scared by the incident? Has reminiscing about this made you want to make contact again? Prey tell, the suspense is killing me!