Your most awkward experience ever?

[rosac]

Everyone's had an awkward experience, from simply calling your teacher mum/mom in primary school or forgetting your shorts for PE and having to wear the minging ones from lost property, so escapist, I ask you: What is your most awkward experience EVER?

Mine is a long one, but here goes:

Me (male) and my girl best friend are at a club, having lost our other friends. She's staying with me to ward off a creepy guy who helped her in the past and wants something in return (not cool). Me and her are dancing with an American footballer, when a guy I don't recognise walks up to her, says something to her, causing her to run off crying.

Right, Ok, bit weird, but I go and find her sitting on the stairs. She then explains that she has a semi-long term boyfriend (first I'd heard about it, and I knew she'd been back with a few different guys the previous months...) and that was his twin brother, who accused her of cheating with the american footballer (50% right, you tried). She's still in floods of tears and hammered, so I suggest she goes home. I walk out with her and go to hail her a taxi (I live in the city centre, she lives a mile or so out), she then stops me and says she wants food, specifically from a kebab shop near where I live. I reluctantly agree, and we go.

On the way, she keeps mentioning how she can't really be bothered to get a taxi, asking if she can stay at mine, how she can't afford it etc. I tell her I'll pay for her taxi, she needs to go to her own home. This makes her cry even more. We get food (getting really odd looks, crying girl + famously sober guy is not good) and I go to get her a taxi again. She then bursts into tears AGAIN and heads off towards my house.

I go and fetch her, and tell her I'll get her a taxi from my house. We get in, and she goes straight into my room, undresses and gets into my bed. She's still crying, very drunk, and I'm stone sober.

I knew there'd be no way I could move her now, so I go and get my sleeping bag and tell her I'm sleeping on the sofa. She cries even more until I decide to sleep in the bed, but fully clothed and as far away from her as possible.

She then moves over, starts spooning me (she was big spoon), kissing me, groping me. Whilst still crying about the fact someone had accused her of cheating. I shook her off, told her to go to sleep, at one point left to go for a shower in the hope she'd nod off and I could escape (from my own bed, she didn't). She then carried on and began to say:

"Oh my god *rosacs name* this must be so awkward for you, I'm so sorry, I'm such a bad friend" WHILST STILL CRYING. I just had to tell her it was fine and shake her off until she went to bed.

It got to the morning, I let her get dressed, gave her a shirt and sent her on her way.

My flatmates then all came out, and in unison said:

"*rosac*, was that really awkward for you? was it a bit awkward."

dickbags.


TLDR: Drunk best friend who was crying as someone called her a cheater came back with me, when I was sober, groped me, kissed me whilst crying, kept asking me if I felt awkward. Flatmates never let me live it down.

Captcha: heat up- yes it did hot up captcha, but not in an ideal manner.

 

[Queen Michael]

We were reading TIME magazine in English class, and I looked at an ad for a wristwatch, and said "This watch gives me the feeling that the wearer's trying to compensate for something."

"What do you mean?" one guy said.

"Well, it feels like whoever's got a watch like this isn't that manly and needs to wear this watch to hide that."

The guy rolled up his sleeve. "I've got a watch like that."

 

[small]

um being busted in the middle of making love by my ex girlfriends mum.. "hi mum, by the way im gay and get OUT"

 

[JoJo]

Once I made a joke about a coworker, then turned around and he was right there looking at me. Hadn't even seen him enter the room. Oops XD

 

[Random Argument Man]

Mine comes in two parts

Context: I only had one real girlfriend in my life. She lived with an over-religious family (not exaggerating the "over" part). We decided to make our relationship serious and push it to the next level. We forgot one detail: we didn't locked the door. Little brother (who's a priest now) barges in.

Actual experience: I was invited to a dinner the following week to meet her parents. The mother was pissed because her daughter got busy out of wedlock and her dad was just pissed because I got busy with his daughter. Little brother kept saying that we would go to hell during the whole dinner. Two weeks later, she broke up with me because her parents made her life a living hell and pretty much told her that they would've kicked her out of the house if she didn't broke things off. They weren't the kind of people to make empty threats.

Good news: she moved out the moment she graduated. She has a kid now and was happy when I last time saw her.
Bad news: pretty much killed any intentions to get a girlfriend for about 3 years. That's how much it was awkward.

 

[Little Woodsman]

Don't know if it's my *most* awkward experience ever, but it happened recently enough that it's stuck in my mind....

At the bus stop where I catch the morning bus for work, there's an older lady (I'm 47 so when I say 'older' I mean she's probably in her mid-fifties) who catches the same bus to her work place. We often chat about how the buses are running, weather... whatever. But I always felt a nagging sense of familiarity about her. Seemed like I definitely knew her from somewhere. Whenever I tried to figure out where I might have known her from I always drew a blank.

Then a few weeks ago we were waiting for the bus and saw a college kid skateboarding against the flow of cars on the street, and started talking about how stupid and crazy that was.

And I said "Well, when you're that age you just do some crazy things."

She replied "Oh yeah, when I was in college I even {giggle} posed for --you know-- {giggle} Playboy."

And suddenly I knew exactly why she seemed so familiar.

Spoiler: somewhat NSFW

I must have spanked to her picture *dozens* of times in my early teens.

It's been a little awkward talking to her in the mornings since then.

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TLDR; Met an older lady, realized that I owned nudie pictures of her from her college days when I was a teen.

 

[Mahorfeus]

You know how everyone in the world supposedly has a doppelganger? Weeeeell...

I was bored one day, so I was sifting through some websites looking for some... explicit material. Nothing really suited my fancy, so I was about to stop when suddenly, an ad for one of those live cams caught my eye. I swear to god, the chick's face looked just like my girlfriend. I noped the hell out of there and played some video games or something.

A few days later I mentioned this to my girlfriend and a good friend of mine for some damn reason. Next thing I know, the three of us are sitting around my computer, journeying through google and the rest of the internet in search of the mystical ad. It didn't help that I couldn't remember the name of the site, so we had to take an awkward dive into my internet search history. After about an hour or so of hitting F5 on a site I happened to recognize, the ad came up. We all took a look at it, agreed that it indeed looked like her, and moved on.

The running joke now is that she has a long-lost porn-star twin sister.

 

[Gizmo1990]

Mine is a two for one deal that I am sure could only happen to me as while I am not that unlucky, when I am it defies all odds.

First my girlfriends mum walks in on us about to do the deed. But Gizmo that is embarrassing sure but not that bad I hear you say and you are right. It was all very uncomfortable, her mum rabled an apology and left the room. Well thats killed the mood so we deside to watch a movie. Just as I am starting the movie we hear my GF's mum scream so we go to see what has happened. And their is my Gf's Sister in bed. With MY Sister. My baby Sister!

Dinner that night was very uncomfortable.

 

[wooty]

One of my mates once walked in on me while I was doggy styling his sister.

Needless to say we didn't speak much after that....

 

[Foolery]

There was this one time at an interview, where the boss had this huge red mark on his face.
I thought maybe he had a small accident of some kind.

So I bluntly asked the guy, "Did you get hit in the face or something recently?"

His dead tone reply was, "No, it's a birthmark."

"..."

And I didn't get the job. 16 year old me was a socially daft moron.

 

[Mikeyfell]

Does having sex with your best friend count? Of course it does.
It was probably much worse for her because she's a lesbian.

The short version is she wanted to sleep with a bisexual girl who she'd been infatuated with for ages.
She agreed but only in a 3 way with a dude, and my friend got the bright idea that it would be easier on her if I was the dude in question.

The worst 3-way ever later I spend about a month worrying that we would never get over how horrible it was.
Happy ending though, those two are still together. so that's good. Totally ruined sex for me though...

 

[Sigmund Av Volsung]

I remember I asked my dad to buy me a chocolate bar once(I was about 6 at the time).

An old woman then looked at me and said "A good beating is what you need". Then turned back around.

That was pretty awkward.

And before someone brings in "child abuse", etc. know that my country has been isolated by the USSR from Western ideas and influences for about 50-odd years. The awkward part was that an old lady said that to a small child out of nowhere, and really angrily too.

 

[L. Declis]

Well, yesterday I was going apartment hunting in China. I was walking around with an agent, and the houses were... not at their best. So I wrote "Jesus Christ, these places are fucking terrible. I could get better by going [competitor agent]."

That was when I realised that I had written it not to my girlfriend... but instead texted it to my agent's phone. The agent who was walking with me.

So I quickly wrote "But thank you for showing me the flats and for your time" and left.

 

[Worgen]

Getting heat stroke when I spent too long going down on a woman in a hot room and almost passing out before I managed to get myself in the shower under cold water. Your move internet.

 

[AnarchistFish]

accidentally kicking this fat woman right in the stomach (really hard) whilst jumping the barrier for the queue for the teacups at thorpe park and having to sit on the ride with her passing me every few seconds in another teacup

 

[Johnny Impact]

http://www.escapistmagazine.com/forums/read/18.858817-Cheating-in-relationships?page=3#21320521

Relevant portion about halfway down.

 

[Vault101]

I would recall but I don't think I remember...probably intentional

I have a terrible aversion to awkwardness....even if I'm watching something on TV and an awkward thing happens I cringe

 

[1Life0Continues]

Back in my much younger days, before I had a clue about tact and sensitivity, I once told a racist joke among some white friends.

Turns out, one of my friends was a mixed race.

Yeah. He was pretty cool about it, but I learned my lesson very quickly.

 

[Silvanus]

I applied to a job that was advertising for bar staff, once. I wrote a bar staff-themed C.V. for the application, got an interview, and headed down there on the train.

I have no idea why, but the job in question had literally nothing to do with bar staff. The job advert had specified that they were looking for bar staff, and yet the position was not even tangentially related to staffing a bar. They were looking for sub-managers in an advertising firm.

Needless to say, I was fairly unprepared for that awkward interview, and did not get the position.