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Jesus, that was awkward

Discussion in 'General Discussion' started by effinshenanigans, Apr 14, 2010.

  1. effinshenanigans

    effinshenanigans
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    As my girlfriend and I were leaving our building to go have dinner at my mom's place last night, my ex--who I haven't spoken to in nearly 3 years after our relationship ended poorly--appeared in front of me. She walked right past the entrance as I was walking down the stairs and I thought to myself, "Yes, please keep walking. You didn't see me. I have sunglasses on. Sunglasses hide all." Then I hear her stop walking and she turns around and says my name in that quizzical and awkward tone people use when they unexpectedly run into someone they don't want to talk to.

    Of course, I mirrored her awkward squawk with one of mine own, hiding the "What the fuck are you doing where I live?" behind "Heyyyyy, how are you?" (If I were a tool, this is where I would've clasped my hands together and bounced them up and down). Of course, my girlfriend is standing right there, so I avoided a potentially damaging faux pas and introduced the two of them immediately. They silently shook hands and we began our inept conversational dance.

    I asked how teaching was going, she asked how my mother was. The whole time each of us were visibly trying to break away from the moment and go on to whatever else we planned on doing; her laughing nervously the whole time, me saying as little as possible and sticking to generalities. About a minute later we thankfully parted, but not before doing that odd bob-in, bob-out where we couldn't decide to give a friendly hug or not, so we just stood there like those inflatable tube people you see at cheesey car dealerships, swaying in the breezes of our inelegant encounter with one another.

    I'm almost never phased by any conversation and I pride myself on my ability to talk to damn near anyone without issue. My girlfriend commented that she had never seen me act so awkward in a conversation and I explained to her that it would've been different if we ran into each other at the local bar that I know she goes to from time to time. I'm actually surprised it hasn't happened already. But to show up where I live just caught me off guard and my normal command of conversation was clouded by the constant thought of, "Where the hell did you come from?"

    Focus:
    We've all had those conversations that, for whatever reason, made us uncomfortable. Sometimes it's with an ex, sometimes your boss catches you putting your balls in the break room coffee pot. What's your story?
     
  2. shegirl

    shegirl
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    Redemption Seeking Whore

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    I once had to tell my boss there was a plane in the hanger. Does that count?
     
  3. deltabelle

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    My ex's dad once asked me what a prostate was. That was awkward. Not as awkward as the time I caught him watching porn though... Not beating it, just sitting there fully clothed, watching.
     
  4. ghettoastronaut

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    An old landlord of mine used to ask me advice about his various erectile dysfunction pills and so forth.

    Nothing breaks your heart like telling an old man that the reason his expensive herbal pills didn't work for him is because they don't work for anyone. Hope he got a prescription for cialis.
     
  5. Diablo

    Diablo
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    I had the same thing happen to me with an ex and the dad watching porn. I came over to drop something off, and when he answered, I could hear the porn blasting in the background...like hardcore porn. I just acted like nothing at all happened and went on doing what I came there to do. The ex and I had a little laugh about it later though.
     
  6. Crown Royal

    Crown Royal
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    This was a shorty, but a goody:

    Back in my drinking-6-nights-a-week days, we frequented this shithole called Carey's on mondays because it was Fanshawe College's booze night there, so hello loose morals. I was jammed up on E and as you probably guessed, trying to make friends with every girl there. I walked up to this dynamite looking brunette sitting alone at the bar, an absolute man-eater-upper. I decide to go with the corniest line possible because I was rolling and didn't give a fuck, and this happened:

    Me: "Do I know you from somewhere?"
    Her: (looking me dead in the eyes) "Do you watch porno?"
    Me: "Umm, sure (dumbfounded beyond comprehension). What's your name?"
    Her: "Slut."

    ......her eyes roll up and....

    CRASH she hits the floor. As it turns out, she was obliterated drunk. Honestly, she didn't LOOK it, but the stool she was on and her elbow were the only thing keeping her ass off the poreclain. The friend that was supposed to be watching her was grinding ass with some guy wearing sunglasses inside because that looks cool. I thought I was going to have a nervous breakdown. I went to she if she was okay and....

    Her: "(VERY UNLADYLIKE WORDS)!!!!!!!"

    Sooo... I walked away. And laughed outside for a few minutes or so.
     
  7. Static

    Static
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    My sister sells sex toys for a living. She's been slowly telling the rest of my conservative-minded family about it one step at a time. I'm finding out firsthand that talking about your sister's sex toy business with ma and pa brings awkward to a whole new level...
     
  8. breakylegg

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    I called in sick one day, and after my girlfriend left, I decided to rent a porn. Later, there was a knock at her door and it was her new, younger female landlord announcing some upcoming construction project. I invited her in but forgot that the porn was on the counter--I think it was called White Trash Whore and on the cover had some blond wearing a plastic pig nose sucking a cock.... Yep, long convo.
     
  9. Gravitas

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    I can think of a few good ones, but this one illustrates what a trainwreck I can be when it comes to picking up girls.

    I was pretty drunk at house party and I was hitting on some random girl. I asked her where she grew up. It was in some shit town and I told her so. She emphatically disagreed and said that it was better than my hometown. We are in New Mexico though, so there isn't exactly a "good" place to grow up.

    Gravitas: Saying your hometown is better than mine is like being the prettiest waitress at Denny's. It doesn't mean much.
    Her: I'm a waitress at Denny's.

    Cue 3 solid seconds of awkward silence until my friend who was listening starts laughing hysterically.
     
  10. Stealth

    Stealth
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  11. cynismus

    cynismus
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    I'm sure I'm not the only one that this has happened to.

    A couple years ago, I hooked up with a textbook slumpbuster. She was bigger than the girls I've dated, had some acne, was a bit obnoxious...the whole package. A couple of weeks after the last encounter, I was out with some of my buddies at a bar and I ran into her. Unbeknownst to me, one of my good buddies knew her from college. So she comes up to me, and the following conversation ensued with a couple of other guys, including the aforementioned one, nearby:

    SlumpBuster: Hey, cynismus! Where have you been? I haven't heard from you in a little while!
    cynismus: Uhh, you know, busy
    SB: Well we should hang out again soon! [flirty (*gag*) wink]
    cynismus: Yeah, see you around

    That was awkward enough. Imagine how fucking bad it was when my buddy that knew her back in the day brought it up with me the next day.

    buddy: Sooo...how do you know SB?
    cynismus: Friend of a friend, really random
    buddy: So, how was the booty? More than you could handle?
    cynismus: Shut the fuck up! If you tell anyone about this, I will stab you in the balls.

    Luckily for me, he's somewhat of a pussy and actually believed that I would cause him bodily harm.
     
  12. Suit Jacket

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    girl: Awkward is your favorite word.
    SJ: And my favorite emotion.
    girl: Awkward is not an emotion.
    SJ: I'm not good with emotions.

    /Suit Jacket is back.
     
  13. lust4life

    lust4life
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    Before we were married, my wife and me were at her parents' house one night while they were out. We rented "Fast Times at Ridgemont High" and were watching it in the TV room. Well, her folks came home early, we didn't get to the VCR fast enough, and they settle in to watch the movie. About 5 minutes after they join us, Phoebe Cates begins to demonstrate the proper technique for fellatio on a piece of produce. My future mother-in-law (a devout Catholic) rises and departs, taking her daughter with her, leaving me with my future father-in-law, the cop.
     
  14. sunny jim

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    Well, you know how many buttons there are on a rabbit, and how hard it is to find the 'off' button when you really need to?
    I do.
     
  15. Mike Ness

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    About three years ago I had to meet a client in Philadelphia late on a Thursday night. He had bought commercial property early in the afternoon and missed signing some documents so I ran down to the city so he could sign them and we could get everything closed.

    I met him at his office and he commented that he and some of the guys he works with just had Mexican (HINT: that's foreshadowing) Anyway It was just he and I in a small conference room in his office, I wasn't even going over the forms he was just signing away.

    I was then taken back by quite possibly one of the worst smells I have ever encountered. Honestly, if you could trap this smell you could rob a bank with it. It was horrific. It was so bad that there was no way I could play it off, I had to turn my head and try and breathe using only my mouth. I looked at the man, he was blushing but he kept his eyes on the FORMS and kept signing! I was praying that he would relieve the tension with a joke or something!

    But no he just stood there while I suffered through his horrible diareah SBD, it was the most uncomfortable two and half minuets of my life.
     
  16. Bogan

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    A few years back my relatively new girlfriend of a few months and I had my house to ourselves for the evening and proceeded to make the most of our time alone. She was in her last year of high school (I'd finished the year before) and still had her uniform on. We'd christemed a few rooms and tested the stability of the pool table and were finishing up with me receiving some head in our rumpus room. This girl was criminally good at blowjobs and after all that had happened I was ready unleash a motherload.

    Cue the sound of the front door opening and 'guys, we're home' from my mother. With perfect timing the girlfriend looks up and says 'oh crap' just as I promptly blow all over the front of her dark blue dress. Holy shit, panic stations. Luckily we were upstairs where she could get a change of clothes from my room and we could clean the dress in the bathroom. Unluckily jizz stains can be quite difficult to get out of clothes, especially navy blue school dresses.

    With no more useful options left upstairs we decided on the washing machine, though this meant we'd have to deal with my folks and the inevitable questions on why we needed to wash her dress. I stammered through the excuse that the dog had pissed on it, which was somewhat believable as the little bugger pissed on everything. Phew, crisis averted. Unfortunately the washing machine wasn't up to the task and the unmistakeable stain hadn't budged.

    My mother then comes to see what I'm doing in the laundry. Thinking quickly I throw the dress in a bucket with stain remover and feebly try to explain that the machine 'didn't get the piss smell out', which received a skecptical look from my mother. While she never said anything, I'm sure she knew. Then I had to take the girlfriend home, though I left her to explain to her folks why she was coming home sans dress. I suppose the lesson here is never stop in the middle of a blowjob.
     
  17. Jimmy James

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    My mom works at a hospital in Honolulu. She generally finished between 10-11 PM and would swing by the apartment she had rented out to me and my brother. I never wanted her there, mostly because two guys in their early twenties that have decided to forgo college and begin working, are generally piss drunk or high as shit. Unfortunately, I was neither of those things as I went down to drop off our rent check.

    I can't remember what lead to the discussion we had. Probably the fact that I was twenty-four and single.

    Imagine your mother nagging you about getting a girlfriend and settling down. After about eight minutes of this, she starts in on the story of my dad and her and how they fell in love. This was weird enough until she tells me the first time she ever had sex, at all, she got knocked up with me.

    I contemplated jumping off the nearest freeway overpass for the next few days.
     
  18. jennitalia

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    Last summer I headed out to my friend's farm for a cattle branding. As is commonplace on farms, they had a lot of cats. His younger brother had named all the cats after various politicians (Barack, Stephen Harper, etc...) One of the cats was bestowed the name of Jack Layton. However, Jack Layton got pregnant and since figuring out Jack was a girl, the young brother decided to change the cat's name to Jackie Layton.

    The first night of the weekend, the girls slept in one tent and the boys in the other. In the middle of the night the guys pulled some shenanigans and I felt something brush up against my face which was pressed into the side of the tent. In the morning I asked what brushed up against my face. One of the guys replied that it was probably just a cat. Not thinking, I blurted out "Oh yeah, sure, JackieLayton on my face!"

    Stay classy, jennitalia.
     
  19. nooneuknow

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    I was probably around 16 when my desktop computer first decided to crap out on me. I believe it had some sort of problem playing videos properly. At the time, a conservative friend of my mother's was the best computer guy we knew. He was a relatively recent immigrant from the old country and led a happy and boring life with his conservative wife.

    After he fixes the problem, he decides to test out the computer. He does this by doing a simple search through my hard drive of all video files. Now, I don't know why he decided to click on pornwhores.mpg (or some similar, very obviously porn, video name), but I'm sure the image of two chicks going at it full screen will forever be burned in his brain. Oh, and my mother was sitting right beside us the entire time. I don't know if I've ever seen a grown man blush like that. Before that night, he knew me as a responsible, gifted, goody-two-shoes daughter. I still see this man at almost every holiday. And the ironic thing is that in my whole life, I've only downloaded porn onto my computer that one time. I was very good at covering my porn tracks up to then.

    In case you were wondering, my mother didn't care too much...she'd been bugging me about getting to know my body for years. You'd think that would be awkward, but I got used to her crazy early on in life.
     
  20. FuckerTax

    FuckerTax
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    My ex-girlfriend's dad walking in as she was giving me a blow job. This was in high school and I was never quite sure if he saw her mouth on my dick but definitely saw her jumping up from her knees with her shirt off... Yeah, I had to break it off shortly after that.

    Edit: After posting I feel that I should elaborate on this.

    As I mentioned, I was in high school and was dating this girl from the local catholic school. To build up some street-cred I feel that I need to add that she was hott as hell. So we were dating for probably 4-5 months. I'm cool with her family. They got to know me pretty well because I was over quite often "watching movies" in the finished basement with their daughter. Every time I was over there I would always feed them a bunch of shit and they LOVED me.

    I used to go over to her house after school about every day and we would fuck around. We usually had about an hour until her dad got home from work. One day we're sitting in her living room, the activities started a little late for some reason and she was very hesitant to blow me because she was afraid her dad would be home. We were in her living room and they had a big picture window that opened up to the long driveway. I explained to her that I would be able to see her dad pulling up if I wasn't finished blowing in her mouth by then and by the time he got in we would be sitting there like well behaved, non-sexually active kids.

    Well, right as I'm about to blow HER FRONT DOOR OPENS. She hops up quicker then I had ever seen anybody move, pulls a blanket over both of us, and we just stare DAZED looking at her father. He just stared at us for a good 3-4 seconds (eternity,) I'm assuming trying to figure out what he just saw.

    Dad: "Why is your shirt off?"
    Slutty Ex: It's not.
    Dad: "It better not be."

    Then he walked away.

    She said that she went into her room and stayed there the rest of the night. I went over there a few other times after that and we never really talked much. But apparently, he nor her mom ever said anything to her about it. However, it was too fucking weird and we broke up like 3 weeks after the incident.