OK.... time to 'fess up to your most cringeworthy moment(s)

[Starchivore]

I tried to think, but I feel like I've repressed all my worse ones. When I search back in my mind, there's this uncomfortable, ominous feeling... but the most awkward memories- which I know are there- just don't come.

Not sure if that's good or bad. Growing up my worst worst fear was always being embarrassed in front of people, in any way at all. That kind of fear is very constricting

 

[Globalti]

Probably the time I met a couple I knew from the pub. Hadn't seen them for a while. "When's the baby due?" I ask. "I'm not pregnant!" she replies.

 

[captain nemo1701]

I work for a large firm with three letters in the title (no - I'm not saying who!). One of them is an 'S'. One day, I found myself talking to a lady who walked into our office looking for our MD. While waiting for him, we got chatting. I asked what job she did in the three -letter firm.

Her reply...'I'm the 'S' .

Little did I know that she was one of the big cheeses who own the firm.... She laughed about it though.

 

[ColinJ]

Oh, go on then!

I got my numbers mixed up...

I stood at the front of a queue at an ice cream van and asked the handsome young Italian guy for a '69', resulting in lots of giggling parents behind me with their kids asking what was so funny!

 

[Dave7]

Oh, go on then!

I got my numbers mixed up...

Did you get one

 

[ColinJ]

Did you get one

A '99' - yes... I grabbed it and ran away from my cackling neighbours!

 

[Vantage]

I was in my early 20's and my mate and I had met some girls through another friend. We'd arranged to go out clubbing and so the beer flowed.
Towards the end of the night and after a slow dance spaz attack with my date, I figured I'd be the gentleman she'd been looking for and asked, "Would you do me the honour of allowing me to kiss you?"
It was bad luck that my mate and his date happened to be right next to us and heard everything. Mate, date and his date all cracked up laughing.
I did get my smooch though, she thought it was cute

It never pans out the way it does in the movies