Most Awkward Moment?

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Gudrests

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Mar 29, 2010
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badgersprite said:
The best story I know actually comes from my parents.

When they'd just started dating, my mother went over to my dad's house and she happened to see a wig in his room. Naturally, she thought this was funny and brought it out, making jokes about why he would need a wig, asking if he was a drag queen or something.

My dad just looked at her and said. "That was my little brother's. He died of leukemia."

...
OMG.....thats amazing...like its sucks ur uncle died but..that moment..for anyone else to hear about is awsome as can be (besides the dying part)

Mst awkuard moment ever wasss....me asking a girl out my first time...i turned around..said UH UH UH UH UH UH UH and then spun back around....sweating bullets....ahhh back when i had no balls...now, its wanna go out..no? OK
 

WorldCritic

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Apr 13, 2009
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Running in to my ex-girlfriend at the mall. A couple awkward stares and then I run away before she gets the chance to call the police.
 

Peteron

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Oct 9, 2009
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Ok, so me and a couple of my friends were hanging outside of the school. Anyway, somehow the conversations turned to midgets and dwarves, and basically I started saying that I wish I had a pet midget so I could dress it up in a clown suit. Apparently, one of the guys' mom was a legal midget, and he pointed it out to me. (He wasn't really a friend) Then I asked him if his mom had a clown costume. There was quite an awkward pause after that.
 

Jimmyjames

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Jan 4, 2008
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At a scholastic conference in high school, I walked in a girl who was getting dressed in her room by accident. I was looking for a friend and I got the wrong dorm room. The girl happened to be someone I liked and she avoided me the rest of the trip. Pretty embarrassing. I think she thought I did it on purpose.
 

TheTurtleMan

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Mar 2, 2010
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Well I know something very awkward that just happened recently. I was in my PE class at school and my friend was letting me borrow his pair of short soccer pants since I had left mine at home. Well it turns out that doing jumping jacks in a pair of loose fitting shorts tends to show a bit more than desired . . . .
 

astrav1

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Jul 6, 2009
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Lullabye said:
Touching penises with another guy.
Really.
Fucking.
Weird.
Jaranja said:
Lullabye said:
Touching penises with another guy.
Really.
Fucking.
Weird.
How did you manage that?

OT: Let's see... I can't even remember. Meeting my girlfriend for the first time after talking on the internet for a few times was pretty awkward for a few hours.
Yes I am interested as well.

OT: Tearing my pants in church.
 

FlyAwayAutumn

Rating: Negative Awesome
May 19, 2009
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lacktheknack said:
"Ooh! What's that?!"

"...My baby."

I refuse to give context for this.
Please?



Anyway the most akward moment I've had is talking smack about somebody then finding out they're right behind me.
 

Aerodyamic

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Aug 14, 2009
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So, I was having this great anal sex last week.

Suddenly, he looks over his shoulder and asks for a reach-around.

AWWWWKWARD! THE MOMENT IS OVER, *****!
 

Elephant Walker19

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Jul 5, 2010
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girl:"you want to see a boob?"

mraustindude19:"no"

mraustindude19:"Is it a man boob?"

girl:"No,its a girl boob"

mraustindude19 in his head:"I hope she doesn't take that out of context."
 

googleit6

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May 12, 2010
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Hmm... When I'm walking with someone for some reason my hand ALWAYS hits their ass as I'm swinging my arm. That can lead to some awkward "Should I say anything or just ignore it?" moments.
 

AwesomePeanutz

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Aug 17, 2010
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Waving at a person who you think you know but is actually a complete stranger.

Also, having to re-adjust your groin while wearing tight pants. Everyone looks at you...
 

zelda2fanboy

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Oct 6, 2009
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Suicide... Memorial... Party... Ex boyfriend... mourning parents... angry threats of violence... Sort of wish I hadn't reminded myself of that experience again. People who were there still refer to it like they were refugees or war buddies. Good lord.
 

HT_Black

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May 1, 2009
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When I was going to deliver a package at my grandmother's, her housekeeper--who I didn't recognize-- greeted me by name, said it had been so long since she'd seen me, and gave me a hug. I managed to get through it gracefully, however.

Another time--that happeend just three mintues ago, actually-- was when I rifle-whipped my little brother in front of my best friend, mom, pop, and their best friend. It was...interesting.
 

supagama

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Jul 25, 2009
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speaking to a girl after there were rumors that we loved eachother. It didn't help that my friend kept blurting out how I loved her ( I didnt ) every 10 seconds.
 

Dags90

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Oct 27, 2009
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In middle school I volunteered at an assisted living center for people with Alzheimer's, one of the patients there was certain I was her grandson. The worst part was that I actually knew her grandson because his brother was dating my sister.
 
Dec 14, 2008
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mraustindude19 said:
girl:"you want to see a boob?"

mraustindude19:"no"

mraustindude19:"Is it a man boob?"

girl:"No,its a girl boob"

mraustindude19 in his head:"I hope she doesn't take that out of context."
Either the girl was rather unattractive, you're an idiot, or context must be added.

OT: Whenever I'm with my friends trying to think of something to say, but I keep getting distracted by ethical, philosophical, or just plain entertaining thoughts. Those silences are so busy with me battling my wandering thoughts that the annnoyance level is on par with the awkwardness.