Okay, top this awkward situation

[NoeL]

Was out with a friend once and had arranged to stay with her at one of her friend's places. I'd had a pretty big crush on her for a while so decided it was time to make a move.

She turned me down. Five minutes later she was hooking up with some guy on the dance floor. Soon after we walked back to her friend's house, and she brought the dude along. I had to listen to them have sex in the next room for half the night. It was pretty awkward. Ruined most of our friendship.

Another time my mum caught me masturbating.
Another time I caught my brother masturbating.
Another time I broke the family computer by downloading too much porn (the hard drive was only 4gb). When he asked me what was in the multitude of zip files I said they were from a program that rips audio CDs to mp3, and that he was free to delete them. I'm sure he had his suspicions, but decided not to look for himself.

Captcha: no dice.

 

[Catfood220]

When I was 13 orso I walked in on my dad eating my mom out at 07:00 AM... Hey dad, I missed my bu....

Yeah, walking in on parents having sex is horrible. When I was ten, I went downstairs for some reason, I can't remember why and saw my parents havin sex on the sofa. The very next day I got "The Talk".

 

[Grape_Bullion]

When I was like 13 I was just sort of staring off into space during math class. I thought of something funny and started laughing, which I'm sure many of you have done. However, my teacher heard my snickering and asked me what was so funny. Like a retard, I decided to describe what I thought was so funny instead of making up something on the fly. And that was "Do you remember that episode of South Park where they go to the rainforest? Well just think if they had gone to the arctic, and there were Eskimos and Kenny died because he got eaten by a whale." Got detention and everyone avoided me for the rest of middle school. Truly the worst time in my life.

 

[Longstreet]

Once when I was 15 or so I ate dinner at a friend. Later that night when I got home, I smelled that my parents had had shoarma for dinner. So without thinking I commented to my dad; "Oh, you guys ate sperm?". The words sound pretty similar in dutch, but nowhere near similar enough that my dad didn't notice.
He even corrected me.
It was pretty horrific.

Not to be offensive or anything, but how fucked up is your dutch? Besides the last letter 'a' at the end it sounds nothing a like.

Guess i gotta contribute to the awkward moment trend going here, lemme think.
There are the usual drunken stupidities of course but since i can't remember anythings from those nights, there is nothing to be awkward about.

Got a good one though.

My ex-girlfriend, like many, had the tendency to sit on my lap. All cool right? well yea of course, except for one small thing. When we were in her parents living room, with her mom, dad AND brother she would also do that, but not in the traditional way, oh no. More in the cowboy style humping way. Face towards me, half lying against me, one leg on one side and the other on the other side.

Not my most comfortable moment.

 

[Johnny Impact]

I got that beat.

When I was in 8th grade, one of the little sluts-in-training in my year wrote a poem involving me masturbating in public. She then gathered over 100 students, and me, and read the poem out loud to us. Apparently someone dared her to do it. I had no idea what was coming, someone literally pulled me into it by the arm without telling me what it was.

 

[Rylot]

How can she be your mother-in-law if your girlfriend is your girlfriend and not your wife. Also that situation is only really awkward if you had a boner.

Technically she's not my mother-in-law yet but for expedience's sake that's what I call her.

Could have been worse...

Your "mother-in-law" (I'm assuming this is your girlfriend's mother. So kudos on your forward thinking!) could have sat down, taken off her top and asked you to decorate HER decolletage!

Keep Austin Weird, fellow Texan (I'm a Dallas-dweller, but don't hold that against me)!

She was joking about that for most of the time, just ewww. I've only been in Texas for about six months so I don't really care about any of the intercity rivalries. Whenever someone makes fun of College Station I just smile and nod.

Snip'eth

You should have flipped it and played your mother-in-law at her own game by staring at her boobs.

...Again, eww.

 

[TheRightToArmBears]

I've told this one here a couple times but here it goes. Out in a club one night absolutely hammered. Last I remember is about 1 am. Few of us go back to my friends house for a couple more drinks. I pour myself a pint of whiskey and my friend looks away, looks back and it's completely gone. So he gives me two pints of water in the hopes that it might help. Then puts me to bed on a mattress on his bedroom floor. Him and his girlfriend are in bed asleep when my moving around wakes the girl up. She tells my mate that I'm awake as I take off my coat, he says I'm just getting ready for bed. Then I whip it out and start pissing on his bed. He throws her out of the way and tackles me to the ground, I'm on my back, piss going everywhere. When I stop I stand up and start taking off my wet clothes. As I'm stood there, bollock naked, his mother runs in to see what's happening and sees my bare arse. I turn to her, smile, giggle, wave and pass out.

Next day I woke up and asked 4 questions.
Where am I?
Why am I naked?
Why am I wet?
What smells like piss?

He fills me in at which point I try to climb out his window to avoid his parents.

Didn't drink for 6 months after that.

Hey, could be worse. One of my mates crapped himself on the way home from a night out once.

The single most awkward experience of my life happened when I was fifteen. We'd gone out to the golf course/beach (in my hometown, the golf course is right by the beach. It's actually kinda nice) to get drunk, and courtesy of my brother I had a 75cl bottle of vodka. Now at the time there was this girl in the group that I'd been full-on in love with for ages, not that I'd told anyone about it. Boy, did that change. I'm not sure why I thought it was sensible, but during Teenage Dirtbag playing out over the speakers, I necked the whole bottle and passed out on a rock. When I awoke I began screaming at the top of my voice 'I LOVE SAAAARRRAAAAAAAAAAHHHHH!!!!!', and things like that for a good while, in between being sick everywhere. I had to be dragged home at 2:30AM, and then I was roused to go to a guitar lesson at 8AM (which I fell asleep in).

I had absolutely no recollection of the entire night, so I was really confused when I met up with my mates later and everyone fell about laughing. People had to explain to my what had happened, and christ, that was awkward. Seeing her again was worse. Eventually things worked out well though, after a couple of drunken incidents and much flirting. I'm not sure I would ever have plucked up the courage to make any kind of sign I liked her otherwise, so was for the best. Sort of.

 

[Kevlar Eater]

I may have something. Of course, it won't top the more awkward stories, but it'll do:

I was about 15 or 16, with the house and computer to myself, mom and sister gone to do whatever it was women did, I dunno. I basically had the computer to myself and since I was young and sexually curious, I went to whatever porn sites I could remember the names of. I finish around an hour before the ladies returned home and when they did, I was called to get the groceries. When I return inside with the first of many loads of groceries my puny arms could handle, I saw my mom and sister laughing at the computer for some reason. I asked what was so funny, and I was told that I left my porn tabs open.

 

[Beffudled Sheep_v1legacy]

I think I might have one. I was 15 years old and it was one of the last times I ever got drunk.

Me and some friends went out and got hammered near an abandoned project. Mostly normal, lots of alcohol, lots of general dicking around and some sex. One of my better friends had his girlfriend with him but he was ignoring her for some girl another friend just picked up on the way. I, being the gentlemen that I am, went over to hang out with her. We talked, joked and had a good time aaaaaannnnnnndddd then we started to drink some more. A lot more.
I don't remember much of anything except people yelling and laughing a lot and going "What the fuck!?"
Later in the morning after everyone had woken up most people were avoiding me and the girl, and the girl was avoiding me and her boyfriend. Some people were cracking jokes and I was confused so I asked what happened.

They told me that I started to piss on the girl and that she was enjoying it, within visual range of the boyfriend, then we mad out a bit and passed out.

Once I was capable of thinking about everything I was embarrassed and ashamed.

I could never be within 100 feet of my friend or that girl again without feeling extremely uncomfortable, awkward and scummy.

One of the reasons why I don't get drunk anymore...

 

[GeneralFungi]

This one barely even registers on the awkward scale in comparison to some of these stories, but it is one of the only stories I can remember at the moment where I felt truly awkward and most of all embarrassed.

Something I've always thought I was pretty good at was diverting harsh criticisms and bouncing back from embarrassing mistakes. I don't do many truly embarrassing things, but usually I try to bounce back with something to lighten the situation. To laugh with the group rather then be laughed at. However, in this one instance it struck a bit close to home...

I was on a school bus talking with a friend of mine sitting next to me. We were discussing my current household and I was explaining to him what our current set up was. Anyways, I was talking about my mother's boyfriend of 1 year and his children. But what should have come out 'My Mom's boyfriend and his kids' instead came out as 'My boyfriend and his kids'. Keep in mind I was 16 at the time and surrounded by a bunch of other guys from my grade.

It's a mistake that happens. My face practically glowed red that moment and the panic that coursed through me literally petrified me. It was a mistake and everyone knew it, but I was caught so off guard by my own mistake I stammered and attempted to laugh it off (in a very loud and forced way) in a meek attempt to bounce back. Looking back on the incident I completely overreacted and should have taken it in stride, but I was in defense mode at the age. I'm not sure if they suspect anything, but if they were already suspicious that would have probably given me away.

 

[TheSteeleStrap]

You know what, I've got nothing. *writes something* Here's a coupon, you win.

 

[Wintermute_v1legacy]

Once upon a time, I had a little problem with my penis. My girlfriend at the time, well, her dad is a urologist. Without my consent, she talked to him about it and he said he would look at it. So I go to his office the next day and he says, in the most monotone voice you can imagine, "alright, let's see what (her name) is playing with."

 

[thejackyl]

Well...

About 2 months ago I was dating this girl and on our second date we decided to go on a double date with my best friend and his wife. We bought some liquor and were going to have a bad movie/video gaming night.

Dinner went fine, we talked and everything seemed normal. My girlfriend was getting a bit flirty, but nothing too awkward.
The movie went in, but no one was really interested in it, so we turned it off less than an hour into it.

We played You Don't Know Jack for about an hour and my friend's wife decided to call it a night. My friend put in Perfect Dark and the three of us played that for a while. He was making a drinking game out of it, which we all played along in my girlfriend was making a sex game out of it, which her and I were saving for later.

Anyways, we play for a while, she stops playing and starts getting handsy with me, so I stop playing, and my friend continues to play by himself. After a long makeout session she lays across my lap, and gives me a blowjob while my best friend is in the same room, within kicking distance of me.

Later after he calls it a night we proceed to have loud sex on his couch... We kept his wife up..., she wasn't happy in the morning. And still haven't heard the end of it form them. I'm surprised they still let me in their apartment.

 

[FalloutJack]

Hercules was never known for his concentration. Congrats on outperforming a mortal god.

 

[Rylot]

Once upon a time, I had a little problem with my penis. My girlfriend at the time, well, her dad is a urologist. Without my consent, she talked to him about it and he said he would look at it. So I go to his office the next day and he says, in the most monotone voice you can imagine, "alright, let's see what (her name) is playing with."

Good God. Why the hell would you ever want to go to your girlfriend's father's medical practice? Could it have gone any better?

 

[Atrocious Joystick]

I was once with a girl on the way home from the club. We stopped at McDonalds because for some cheeseburgers. She starts telling one of the black employees that was sweeping the floor all this junk about how she believes in his struggle and all that shit. The thing is this is Sweden. And she told him all this in english. Because why would a black guy know Swedish? I became extremely interested in something outside the window and then I got the fuck out of dodge.

I've also been pissed on. Nothing beats waking up to a fresh batch of urine all up in your grill from your half-awake shitfaced pal.

 

[TheNewGuy]

Now it's worth mentioning that my girlfriend was working the same booth with maybe twenty or so other volunteers and fifteen or so painting stations. But I wasn't going to just sit there and start drooling and she knows I'm not the cheating type so she didn't really care and I just went about trying to paint a Spider-man face on a squirming three year old number seven. However the situation reached sitcom levels of contrived awkwardness when my mother-in-law came over to my station. The sheer amount of concentration it took to keep my eyes on the Dachshunds I was painting on my mother-in-law while not sneaking a peek at the flower bosom not more than five feet away was damn near Herculean. The best part was the my Mother-in-Law knew exactly what was going on so she was teasing me the whole time. Definitely the most awkward situation I've been in.

Now a person who was sufficiently talented or motivated might use that situation to set up a nice mother/daughter threesome, and you just go and squander it. Bah! What a waste.

Surprisingly I've never really had that much awkward happen to me, at least not much that I can recall right now, although I may have just repressed those memories.

 

[Gottesstrafe]

Not to diminish the height of your awkward situation, but...


Anyway, my turn. This all starts during one of my better bowel movements in the men's bathroom of a university dorm I was staying in. The night was long, the air was cold, and I was alone save for a paperback novel. It was then I heard a pair of hushed voices walk in and stop in front of the sink, one male and one female. I didn't think much of it at the time, and instead returned to the sordid tale spread before my eyes as my cheeks prepared to spread one final time. That is, until I heard the female one say distinctly "Are you sure you checked the showers? Under the stalls?" "Relax." replied the male voice, "We're good." Not sure whether or not to speak out loud, I prepared to recant the male voice's statement, when I was interrupted by the telltale sounds of pent up carnal desires finally finding release. Awkwardly, I sat silently on my porcelain throne, my utterance preceded and rectum clenched. After what seemed like hours, the moans drifted off into the showers at the other end of the bathroom, followed by the sounds of rushing water as one of the showers must've been turned on. Judging the time right, I proceeded to finish my movement, wiped, and pulled up my pants. Automatic flushing took over, and as I exited to tip-toe to the sink and out the door I was met by the two interlopers peering around the corner to see what was making such a racket. Recognizing their faces (neither of them lived in the dorm building, for the record), I then washed my hands, turned to the door, and called out behind me "See you in class tomorrow."

A few weeks later (also a late night while I was alone in the common room), I returned to the laundry room to retrieve my clothes from the dryer. Pausing outside the door, I was once again graced by the telltale sounds of furious humping (very different sound from the washer, mind you) and moans of delight. Thinking better of it, I then turned around and resolved to pick up my laundry in the morning.

 

[James Joseph Emerald]

A few weeks later (also a late night while I was alone in the common room), I returned to the laundry room to retrieve my clothes from the dryer. Pausing outside the door, I was once again graced by the telltale sounds of furious humping (very different sound from the washer, mind you) and moans of delight. Thinking better of it, I then turned around and resolved to pick up my laundry in the morning.

It would be so funny if just by mere coincidence you happened to be around every time that same couple went dogging.
I mean, how dedicated of a perv would you have to be to manage that?

Once upon a time, I had a little problem with my penis. My girlfriend at the time, well, her dad is a urologist. Without my consent, she talked to him about it and he said he would look at it. So I go to his office the next day and he says, in the most monotone voice you can imagine, "alright, let's see what (her name) is playing with."

Why would you agree to let your girlfriend's dad tinker with your winky in the first place?
Cool username, by the way.