What's your 'most awkward' situation you've been in?

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Well, today, i was...involved in something pretty akward but rather funny i think. I was heading to the bathroom after lunch with a bunch of my friends. I walked in, and apparently, a teacher had walked in right behind me, which I was not aware of. So, i unzip my jeans, and decide to crack the joke from SuperBad. I said "Hey, Brett, come here!! My dick wont shake itself!" Much to my horror, i hear from the stall next to me a deep voice saying "Do you really think thats appropriate for school?" My friends bust out laughing, yet trying to hold it in at the same time, and we all leave ASAP. What makes it worse, is he HAD to see who i was, because I was wearing my letter jacket, with my name emblazened on the back! But looking back, i think its pretty funny, but definately akward!
So, whats a particularly akward moment for you? Anything besides the typical diaper confrontation with the parents would be good to, because many of us have already been there, and know its very, very akward!
 
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Coming out to a girl, that ended up liking me....yeah.....not fun.
 

TallestBabyEver

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lol walked in on someone pissing in the hotel parking garage where I work at...kept saying sorry so i said "don't tell me sorry, tell him," pointing at the security guard behind me:eek:
 

Pojo

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Walking in Wal-Mart with a friend, saying in a deep Satanic type voice "MP3 Players!" and then finding out there were people near by, and my friend saying that they looked scared
 
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I wasnt thinking and I said a "Your momma" joke to a friend but like two weeks before his mom had passed away, there was this really really awkward moment of silence. I felt terrible about it : (
 

satyrical

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Wow, that's a lot of awkward.

When I worked as a Don in a university residence, there were a handful of times when I interrupted residents having sex because they were being too loud...
 

Pojo

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I'm choc full of these moments...Here's another (Mandi knows it)...So me and the same friend and before went to go see Get Smart...Well at the end credits, they played 4 Minutes by Madonna, so we are singing it on the way out...And of course there are people outside that hear and see us...So that was pretty embarrassing...We were laughing like the whole way out...That's like the most embarrassing thing ever
 

RubixFox

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I once walked in while my brother was in the shower. I was like "My eyes"
 

mm3

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My brother found my PSP on the top banister of the stair case, and turned it on -- just happened to stumble upon the videos section... hint. And, the worst part, it was TB related.

I don't keep anything on my PSP anymore.
 

Boogeyman

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My mom walked in on me wacking it... and told me to take out the trash when I was done.
 

Trevor

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My mom walked in on me wacking it... and told me to take out the trash when I was done.

Let me know if she ever signs up for the forum here, I'd like to give her some positive rep for her composure ;)

As for me, it's a long list, but I guess one of the more recent ones was when someone I had a professional relationship with assumed that since I had recommended her work to others and that I had been consistently friendly to her when we had worked together that I was interested in her romantically (not just that maybe I could be, but that I definitely was, and she was ready to roll) It took a couple long, unpleasant phone calls to disabuse her of this notion.
 

tom

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I wasnt thinking and I said a "Your momma" joke to a friend but like two weeks before his mom had passed away, there was this really really awkward moment of silence. I felt terrible about it : (

I also was in a similar situation when cracking a 'your mum' joke. My dad asked me what I had had to eat that night.., I said 'your mum'. His mum had just passed away a month or two previously. :S It was just a reflex reply, I really need to think more sometimes.:S
 

Vaultin

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Dealing with a friend's mother's struggle with cancer, dealing with my grandmother's Alzheimer's...illnesses are awkard.
 

Charlie

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Walking in on two people having sex, one of them being a family friend who I've known for years, as well as being a co-worker.

I often say daft things in social situations that result in awkwardness... I was once bitching to my friend at a party about this guy we knew who really annoyed me. I never said his name, I was mainly attacking the group he was a part of but really it was mainly him I didn't like. When I rant about something, I tend to go way over the top (because I find it funny), so I was really laying into him saying some harsh and unjustified things.
The awkwardness came when he interrupted me inquiring into what I was saying, making me realise that I had been sitting next to him the whole time. >_<
I managed to blag my way out of it, claiming I was talking about some other people.
 

Footed P.J.

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I've never had a non-awkward moment in my life. Even posting in this thread is awkward for me. My breakfast of blackberry toast and bran flakes was awkward. I'm awkwardly listening to Fox News Channel. When will it ever end?!?!!!!!!!?!!!!!1111111oneoneunoeineen
 
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I was in class and I yelled at the computer I was working on "This piece of crap is so gay it deleted my freaking file!" anyway it just so happeened that my teacher was the one openly homosexual teacher at my school : / (That was a long time ago in 7th grade when I was more of an idiot than I am today. And no I wasnt attacking gay/lesbians in any way I just had a limited vocabulary back then)
 
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I was working the overnight shift at a gas station between semesters of college and had just finished taping on a diaper. I was about to pull on my pants, when I heard my bedroom doorknob rattle as someone went to open it. I quickly sat down and held my pants over my lap as my mom came in. We talked for a few minutes, me sitting there wearing just a diaper with my pants trying to cover the diaper. If she saw anything, she never said anything.
 
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