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Old 02-17-2010, 07:04 PM   #1
BroncoMan4ever
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Default Awkward Moments in life

Reading the bill of rights thread and seeing about the awkwardness of using the word Gay around someone who is homosexual, gave me the idea to create a thread in which we can discuss and share a few laughs about our own personal awkward moments that at the time were terrible, but after time passes you see them as interesting or even funny.

My most awkward moment came my freshman year in college. i was working as a manager at a video store. the store was looking to hire a new clerk and I was going through applications with another guy who worked there. we are joking around talking about girls who applied and just having a typical guy conversation.

as I am going through the applications I come across one from a girl who I had been trying to hookup with since high school. so in the continuation of our conversation i turn to my coworker and say "I think I have found the girl we are going to hire." i pass him the application and he looks it over and asks "Why" and being a guy, i tell him "I have been trying to nail this girl since my junior year in high school." to which he replies, "dude that's my cousin."

needless to say the rest of our shift was strange and spent mostly in silence.

side note, i still hired his cousin, and hooked up with her.
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Old 02-17-2010, 07:24 PM   #2
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Nice.

Well I had one of my best friend's sister, who also happened to be another friend's ex-wife, try to hook up with me at a club. She was doing this all infront of her new boyfriend, who didn't think it was cute at all. So as the night goes on he keeps throwing me dirty looks and stupid stuff like that. In bad judgement, I turn my head away from him for a sec to talk to another friend and this punk rushes me. I catch him right before he gets to me and the bouncers throw him out.

I tell both of my friends about what happened and they laugh at this guys stupidity. I explain that I wasn't going to sleep with their sister/ex.

About a month later my friend and his ex get back together. I go over with her brother and watch a fight, just like the old days.

Well the subject of that night comes up, and she says infront of her brother and her man..." You should of come out after, because I was going to **** you that night"

I just kept quiet because I didn't know what to say to that.
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Old 02-17-2010, 09:54 PM   #3
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I was Christmas shopping with my wife at a big department store, she was standing right behind me when I noticed a table full of skimpy ladies thongs. I was messing with them and I grabbed one and said this would be fun because when I was done I could floss with it. When I turned around the lady I was talking to was not my wife, and she was no where in sight. The lady turned about five shades of red and moved on down the isle. I made a bee line to the parking lot and just knew security would be knocking on my window any minute. My wife couldn't stop laughing all the way home....
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Old 02-17-2010, 11:27 PM   #4
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I was Christmas shopping with my wife at a big department store, she was standing right behind me when I noticed a table full of skimpy ladies thongs. I was messing with them and I grabbed one and said this would be fun because when I was done I could floss with it. When I turned around the lady I was talking to was not my wife, and she was no where in sight. The lady turned about five shades of red and moved on down the isle. I made a bee line to the parking lot and just knew security would be knocking on my window any minute. My wife couldn't stop laughing all the way home....
that is messed up. did security come at you?
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Old 02-17-2010, 11:35 PM   #5
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A few years back I got really hammered at my friends house (normal weekend behavior) and his GF breaks out a camera. So my buddy tells her to strip, and she does. But with the caveat that me and my friend strip down too. I did not agree to this, but when you are drunk saying things like No just dont happen. So she is completely nude. He gets completely nude. I get completely nude. We do crazy unexpected things, like playing guitar hero naked, and pictures are being taken all over the place. Events are not exactly clear, so I am not entirely sure what exactly went down in its entirety. I woke up the next morning first, on the floor, still butt naked, with my head in a full ashtray and one sock on my left foot. I go shower, get dressed and sit on the couch, very very confused. My buddy gets up, sits on his end of the couch and neither of us spoke for 45 minutes. I am pretty sure I had a 3 way with another guy and a girl, but its not something I want to ask.

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Old 02-18-2010, 12:09 AM   #6
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A few years back I got really hammered at my friends house (normal weekend behavior) and his GF breaks out a camera. So my buddy tells her to strip, and she does. But with the caveat that me and my friend strip down too. I did not agree to this, but when you are drunk saying things like No just dont happen. So she is completely nude. He gets completely nude. I get completely nude. We do crazy unexpected things, like playing guitar hero naked, and pictures are being taken all over the place. Events are not exactly clear, so I am not entirely sure what exactly went down in its entirety. I woke up the next morning first, on the floor, still butt naked, with my head in a full ashtray and one sock on my left foot. I go shower, get dressed and sit on the couch, very very confused. My buddy gets up, sits on his end of the couch and neither of us spoke for 45 minutes. I am pretty sure I had a 3 way with another guy and a girl, but its not something I want to ask.



I can just see you and your friend sitting in silence on the couch. It's probably best you never mention it again.

My best friend, I've known him for 35 years, is a player. Always has been and always will be. He's always bragged about the chicks he picks up, the raunchy sex acts, etc. He finally settles down a few years ago with a hottie. The two of them are basically sex addicts so they make a good pair. One night I went to their house and had dinner with them. We broke out a couple of bottles of wine, some Jamison, good smoke and got loaded. I passed out, woke up early in the morning and took off.

Strangely, I don't hear from my friend for a week or so, but I don't think anything of it. Finally he calls me but I can tell he's mad. Apparently, in the middle of some drunken sex, his girl starts asking him if he wants a three way. Thinking she means with another girl, he's all for it. Next thing he knows, she's telling him to go wake me up and bring into bed. He got PISSED OFF.

Even though a week had passed, he was still mad. He started interogating me asking if she ever hit on me, if I ever hit on her. It really shook him up. I was completely innocent, didn't know anything about it, but he somehow blamed me like I was the one who initiated it. It took him a couple of weeks to chill out. They're still together and now it's always awkward when we're around.
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Old 02-18-2010, 12:59 AM   #7
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My mother walked in on me having sex with a girl in my walk in closet when I was 15.

Worst.

Experience.

Ever.
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Old 02-18-2010, 02:05 AM   #8
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My mother walked in on me having sex with a girl in my walk in closet when I was 15.

Worst.

Experience.

Ever.
i accidentally got a hummer from my high school girlfriends mom.

it went down like this. during our spring break my girlfriend and her family were going up to the mountains to ski for the break. we had been dating for like 6 months so she invited me to go with them. they had relatives who had a nice house near where we were skiing and snowboarding for the week. We got there and the rules were obviously, at night i stay in my room and my girlfriend in hers. no funny business allowed, but we were teenagers, so naturally we were going to break the rules anyway.

first few days are awesome, snowboarding and going at it like rabbits every chance we got. midway through the week we were up there, her mom and dad start fighting like crazy. they decide they were going to spend the rest of their vacation in separate rooms.

so first night they are apart is no big deal, but the next day as i am getting ready to crash for the night, my girlfriends dad comes into my room and asks if we can switch because the bed in the room he was staying was hurting his back. so naturally i agree and trade rooms with him. so i fall asleep in the new bed and midway through the night i wake up to the feeling of what i thought was my girlfriend giving me a hummer. so i am laying there enjoying what is going down and i tell her in these exact words "we need to do this fast, so that your parents don't catch us."

the minute i say that the hummer stops, and she gets up to turn on the lights in the room. as soon as she does, and i realize its her mom, we both basically have that look on our faces saying wtf just happened here?

the last 2 days were extremely uncomfortable. the girlfriend and i went about our usual business and just moved on. i am a guy and at the time 17 so naturally any hummer was a good thing, so i was happy and didn't care that it was from her mom and just acted like nothing happened. but her mom was a freak. always pulling me aside saying how we need to say what happened and ask her husband and my girlfriend to forgive us. i keep telling her no and just forget it and move on, but finally she snaps on the last night we were there and blurts out what happened.

needless to say the drive back home was the longest most miserable drive of my life. my now ex girlfriend and myself sitting in the backseat with her either looking at me or her mom disgusted or screaming at me for letting it happen. when her arguments 1st started i tried telling her the truth. i was asleep and her mom jumped on my junk and in the dark room at night i didn't see that it wasn;t her. but as all guys know, most arguments with ladies you aren't going to win, no matter what you say or if it really wasn't your fault. in addition to the ex biting my head off, i have her father, eyeballing me in the rear view mirror and her mother who won't shut the hell up, trying to smooth things over, saying how it was harmless and just an accident and that we should all just move on(which for the 2 days prior i was telling her to do herself so we could have avoided the entire mess)

so finally after what seemed like an eternity we get back home. sadly the ordeal didn't end when we got back home.

the ex was constantly calling and hasseling me, and told her friends who in turn also called to give me ****. she returned my letterman's jacket, but with burn marks and holes cut into it. her parents a few months later got divorced, and according to her friends and family, it was all my fault. and to add to the weirdness. her mom called my mom, to tell her what happened between us. so not only did i have to deal with the ex, her friends and parents, but also my mom for a few months giving me strange looks and giving me **** for it all the time

easily the strangest time of my life.

Last edited by BroncoMan4ever; 02-18-2010 at 02:08 AM..
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Old 02-18-2010, 02:06 AM   #9
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These should be done in MS Paint format.
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Old 02-18-2010, 04:24 AM   #10
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when i was in highschool i worked at sears part time, a girl i worked with asked me if i ever had mrs duffy as a teacher, i said no i hadnt but i hear shes a real b****, she nods agrees and then says "shes my mom"
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Old 02-18-2010, 05:32 AM   #11
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i accidentally got a hummer from my high school girlfriends mom....her parents a few months later got divorced, and according to her friends and family, it was all my fault.
Home wrecker!

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Old 02-18-2010, 06:18 AM   #12
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I work at an accounting firm and one day we got this new intern for the summer. I was his counselor so it was my job to take him around to introduce him to everybody. The thing about this intern is he only had one arm. On the other side was just a nub. More on that later.

So I take him to this manager's cube to introduce him and you can tell that this manager is really trying not to stare at the nub. So I try getting some small talk going. I had a poker game planned for that weekend and asked the manager if he was going to be able to make it because he had said earlier in the week that he had a lot of yard work to do. To which he replies "I don't think I can make it man, not unless I grow an extra set of hands."... Awkward.

Nice way to introduce the kid to the corporate world.

Last edited by Bronco Boy; 02-18-2010 at 06:21 AM..
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Old 02-18-2010, 06:23 AM   #13
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Originally Posted by BroncoMan4ever View Post
i accidentally got a hummer from my high school girlfriends mom.

it went down like this. during our spring break my girlfriend and her family were going up to the mountains to ski for the break. we had been dating for like 6 months so she invited me to go with them. they had relatives who had a nice house near where we were skiing and snowboarding for the week. We got there and the rules were obviously, at night i stay in my room and my girlfriend in hers. no funny business allowed, but we were teenagers, so naturally we were going to break the rules anyway.

first few days are awesome, snowboarding and going at it like rabbits every chance we got. midway through the week we were up there, her mom and dad start fighting like crazy. they decide they were going to spend the rest of their vacation in separate rooms.

so first night they are apart is no big deal, but the next day as i am getting ready to crash for the night, my girlfriends dad comes into my room and asks if we can switch because the bed in the room he was staying was hurting his back. so naturally i agree and trade rooms with him. so i fall asleep in the new bed and midway through the night i wake up to the feeling of what i thought was my girlfriend giving me a hummer. so i am laying there enjoying what is going down and i tell her in these exact words "we need to do this fast, so that your parents don't catch us."

the minute i say that the hummer stops, and she gets up to turn on the lights in the room. as soon as she does, and i realize its her mom, we both basically have that look on our faces saying wtf just happened here?

the last 2 days were extremely uncomfortable. the girlfriend and i went about our usual business and just moved on. i am a guy and at the time 17 so naturally any hummer was a good thing, so i was happy and didn't care that it was from her mom and just acted like nothing happened. but her mom was a freak. always pulling me aside saying how we need to say what happened and ask her husband and my girlfriend to forgive us. i keep telling her no and just forget it and move on, but finally she snaps on the last night we were there and blurts out what happened.

needless to say the drive back home was the longest most miserable drive of my life. my now ex girlfriend and myself sitting in the backseat with her either looking at me or her mom disgusted or screaming at me for letting it happen. when her arguments 1st started i tried telling her the truth. i was asleep and her mom jumped on my junk and in the dark room at night i didn't see that it wasn;t her. but as all guys know, most arguments with ladies you aren't going to win, no matter what you say or if it really wasn't your fault. in addition to the ex biting my head off, i have her father, eyeballing me in the rear view mirror and her mother who won't shut the hell up, trying to smooth things over, saying how it was harmless and just an accident and that we should all just move on(which for the 2 days prior i was telling her to do herself so we could have avoided the entire mess)

so finally after what seemed like an eternity we get back home. sadly the ordeal didn't end when we got back home.

the ex was constantly calling and hasseling me, and told her friends who in turn also called to give me ****. she returned my letterman's jacket, but with burn marks and holes cut into it. her parents a few months later got divorced, and according to her friends and family, it was all my fault. and to add to the weirdness. her mom called my mom, to tell her what happened between us. so not only did i have to deal with the ex, her friends and parents, but also my mom for a few months giving me strange looks and giving me **** for it all the time

easily the strangest time of my life.
I would regret that I said anything while the BJ was going down.
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Old 02-18-2010, 07:05 AM   #14
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Quote:
Originally Posted by BroncoMan4ever View Post
i accidentally got a hummer from my high school girlfriends mom.

it went down like this. during our spring break my girlfriend and her family were going up to the mountains to ski for the break. we had been dating for like 6 months so she invited me to go with them. they had relatives who had a nice house near where we were skiing and snowboarding for the week. We got there and the rules were obviously, at night i stay in my room and my girlfriend in hers. no funny business allowed, but we were teenagers, so naturally we were going to break the rules anyway.

first few days are awesome, snowboarding and going at it like rabbits every chance we got. midway through the week we were up there, her mom and dad start fighting like crazy. they decide they were going to spend the rest of their vacation in separate rooms.

so first night they are apart is no big deal, but the next day as i am getting ready to crash for the night, my girlfriends dad comes into my room and asks if we can switch because the bed in the room he was staying was hurting his back. so naturally i agree and trade rooms with him. so i fall asleep in the new bed and midway through the night i wake up to the feeling of what i thought was my girlfriend giving me a hummer. so i am laying there enjoying what is going down and i tell her in these exact words "we need to do this fast, so that your parents don't catch us."

the minute i say that the hummer stops, and she gets up to turn on the lights in the room. as soon as she does, and i realize its her mom, we both basically have that look on our faces saying wtf just happened here?

the last 2 days were extremely uncomfortable. the girlfriend and i went about our usual business and just moved on. i am a guy and at the time 17 so naturally any hummer was a good thing, so i was happy and didn't care that it was from her mom and just acted like nothing happened. but her mom was a freak. always pulling me aside saying how we need to say what happened and ask her husband and my girlfriend to forgive us. i keep telling her no and just forget it and move on, but finally she snaps on the last night we were there and blurts out what happened.

needless to say the drive back home was the longest most miserable drive of my life. my now ex girlfriend and myself sitting in the backseat with her either looking at me or her mom disgusted or screaming at me for letting it happen. when her arguments 1st started i tried telling her the truth. i was asleep and her mom jumped on my junk and in the dark room at night i didn't see that it wasn;t her. but as all guys know, most arguments with ladies you aren't going to win, no matter what you say or if it really wasn't your fault. in addition to the ex biting my head off, i have her father, eyeballing me in the rear view mirror and her mother who won't shut the hell up, trying to smooth things over, saying how it was harmless and just an accident and that we should all just move on(which for the 2 days prior i was telling her to do herself so we could have avoided the entire mess)

so finally after what seemed like an eternity we get back home. sadly the ordeal didn't end when we got back home.

the ex was constantly calling and hasseling me, and told her friends who in turn also called to give me ****. she returned my letterman's jacket, but with burn marks and holes cut into it. her parents a few months later got divorced, and according to her friends and family, it was all my fault. and to add to the weirdness. her mom called my mom, to tell her what happened between us. so not only did i have to deal with the ex, her friends and parents, but also my mom for a few months giving me strange looks and giving me **** for it all the time

easily the strangest time of my life.
Epic.
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Old 02-18-2010, 07:10 AM   #15
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The real question is: who gave the better bj? The girlfriend or the mom?
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Old 02-18-2010, 07:13 AM   #16
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Originally Posted by sirhcyennek81 View Post
A few years back I got really hammered at my friends house (normal weekend behavior) and his GF breaks out a camera. So my buddy tells her to strip, and she does. But with the caveat that me and my friend strip down too. I did not agree to this, but when you are drunk saying things like No just dont happen. So she is completely nude. He gets completely nude. I get completely nude. We do crazy unexpected things, like playing guitar hero naked, and pictures are being taken all over the place. Events are not exactly clear, so I am not entirely sure what exactly went down in its entirety. I woke up the next morning first, on the floor, still butt naked, with my head in a full ashtray and one sock on my left foot. I go shower, get dressed and sit on the couch, very very confused. My buddy gets up, sits on his end of the couch and neither of us spoke for 45 minutes. I am pretty sure I had a 3 way with another guy and a girl, but its not something I want to ask.



haha...you crossed swords.
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Old 02-18-2010, 07:18 AM   #17
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Originally Posted by BroncoMan4ever View Post
i accidentally got a hummer from my high school girlfriends mom.

it went down like this. during our spring break my girlfriend and her family were going up to the mountains to ski for the break. we had been dating for like 6 months so she invited me to go with them. they had relatives who had a nice house near where we were skiing and snowboarding for the week. We got there and the rules were obviously, at night i stay in my room and my girlfriend in hers. no funny business allowed, but we were teenagers, so naturally we were going to break the rules anyway.

first few days are awesome, snowboarding and going at it like rabbits every chance we got. midway through the week we were up there, her mom and dad start fighting like crazy. they decide they were going to spend the rest of their vacation in separate rooms.

so first night they are apart is no big deal, but the next day as i am getting ready to crash for the night, my girlfriends dad comes into my room and asks if we can switch because the bed in the room he was staying was hurting his back. so naturally i agree and trade rooms with him. so i fall asleep in the new bed and midway through the night i wake up to the feeling of what i thought was my girlfriend giving me a hummer. so i am laying there enjoying what is going down and i tell her in these exact words "we need to do this fast, so that your parents don't catch us."

the minute i say that the hummer stops, and she gets up to turn on the lights in the room. as soon as she does, and i realize its her mom, we both basically have that look on our faces saying wtf just happened here?

the last 2 days were extremely uncomfortable. the girlfriend and i went about our usual business and just moved on. i am a guy and at the time 17 so naturally any hummer was a good thing, so i was happy and didn't care that it was from her mom and just acted like nothing happened. but her mom was a freak. always pulling me aside saying how we need to say what happened and ask her husband and my girlfriend to forgive us. i keep telling her no and just forget it and move on, but finally she snaps on the last night we were there and blurts out what happened.

needless to say the drive back home was the longest most miserable drive of my life. my now ex girlfriend and myself sitting in the backseat with her either looking at me or her mom disgusted or screaming at me for letting it happen. when her arguments 1st started i tried telling her the truth. i was asleep and her mom jumped on my junk and in the dark room at night i didn't see that it wasn;t her. but as all guys know, most arguments with ladies you aren't going to win, no matter what you say or if it really wasn't your fault. in addition to the ex biting my head off, i have her father, eyeballing me in the rear view mirror and her mother who won't shut the hell up, trying to smooth things over, saying how it was harmless and just an accident and that we should all just move on(which for the 2 days prior i was telling her to do herself so we could have avoided the entire mess)

so finally after what seemed like an eternity we get back home. sadly the ordeal didn't end when we got back home.

the ex was constantly calling and hasseling me, and told her friends who in turn also called to give me ****. she returned my letterman's jacket, but with burn marks and holes cut into it. her parents a few months later got divorced, and according to her friends and family, it was all my fault. and to add to the weirdness. her mom called my mom, to tell her what happened between us. so not only did i have to deal with the ex, her friends and parents, but also my mom for a few months giving me strange looks and giving me **** for it all the time

easily the strangest time of my life.

It's funny that people would blame their failed marriage on you. People are funny.
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Old 02-18-2010, 07:30 AM   #18
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I have a decent one.

I used to work for this one company doing software development and we were subcontractors for another company who were the prime contractors. This other company was right next to us so we often went over to have meetings, etc. Well, as soon as you walk in, there was a cute little secretary. She was 19/20 or so (I was 22 at the time). I didn't think much of it, at least any more than just eye candy going in and out of their offices. Eventually we started talking, initially just about work but then it became more social. Then we had a company happy hour and I was able to talk to her more. We started flirting here and there when I was over in her offices and over IM but I didn't really think much of it. Well one day I walk into my office and there was mail on my desk from the other company which was quite routine since all of the documentation came from them. It was an interoffice mail envelope, the kind that has signatures on it of the people who have received it and passed it on, etc... I opened up the envelope to find a pair of panties. Naturally I was confused initially, but there was also a letter in the envelope which read "I'm not wearing panties right now, what are you going to do about it?". At this point, being a 22 year old male, I'm in awe. I started to think to myself that this obviously came from the secretary chick but I didn't know her handwriting. So I talk to her on IM right then just to see if she says something about it but nothing ever came up. I'm somewhat boggled because I thought for sure she'd say something so maybe it wasn't from her. Well at lunch I found out. She came down into my office at lunch time and shut the door. She's like, "I see you got my envelope" and promptly pulled up her mini-skirt baring her private area. At this point I'm barely able to talk because I feel like this is a porn movie or something because these types of events rarely happen in life, especially to me. Regardless, I'm going to run with it. We proceeded to have sex in my office right then and there. That was the beginning of many encounters in my office both at lunch time and after work for a good 6-8 months until she finally wanted something more serious and she became real clingy. It was definitely awesome while it lasted.

On a side note: Since most of my friends wouldn't believe the story, I brought the "inter-office" mail envelope home and kept it as proof. Well years later after it was in the bottom of an unused drawer, my current girlfriend found it and completely flipped out. I had to explain the whole situation to her and that it was years ago. But on a good note, she now feels obligated to out-do that situation...
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Old 02-18-2010, 07:31 AM   #19
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I ran into an old G/F from HS about 3 years after we both graduated. She had put on about 20 to 30 lbs, all in her belly. I congratulated her and asked her when she was due. She gave me a drop dead look and announced she wasnt pregnant.

And while this isnt as cool as getting BJs from your G/Fs mom, I HIGHLY recommend never talking to a chick about being pregnant unless she brings it up.
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Old 02-18-2010, 07:38 AM   #20
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Quote:
Originally Posted by loborugger View Post
And while this isnt as cool as getting BJs from your G/Fs mom......
I think it's a safe bet that 99% of the posts from here on out could probably start with this disclaimer....
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Old 02-18-2010, 07:41 AM   #21
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He's lucky it wasn't her dad....
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Old 02-18-2010, 07:44 AM   #22
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No way Mom didn't know who she was giving the hummer too.
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Old 02-18-2010, 08:10 AM   #23
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Quote:
Originally Posted by loborugger View Post
I ran into an old G/F from HS about 3 years after we both graduated. She had put on about 20 to 30 lbs, all in her belly. I congratulated her and asked her when she was due. She gave me a drop dead look and announced she wasnt pregnant.

And while this isnt as cool as getting BJs from your G/Fs mom, I HIGHLY recommend never talking to a chick about being pregnant unless she brings it up.
I am never the first to mention being pregnant to any woman, even if the baby's crowning and I have the southern view to confirm it. It just goes awkward so often it ain't worth it. If she says she's pregnant, fine. Other than that, uh uh, no way.
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Old 02-18-2010, 08:31 AM   #24
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okay guys, catch this.

This particular event happened last summer on my uncle's farm in Virginia. My brother and I had just finished cutting a field of hay and were enjoying the evening meal under the shade of an elm tree. He went down for water by the creek and when he was gone, I took a bowl that was filled with delicious plum pudding and placed into it, not one, but two large pieces of sheep s***. When he returned I encouraged him to taste the plum pudding... And as sure as Im standing before you, he did! He ate it all. S*** Pudding!



Edwards: You got your brother to eat sheep dung. That is a very interesting story.

Hunt: Tell him the ending, that's the best part.

Higgins: Oh yeah. To be perfectly honest with you sir, I have no brother. It was me. I ate sheep S***! Swear to God! it was Me!
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Old 02-18-2010, 08:36 AM   #25
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I'd be shocked if more than 5 people here knew what movie that quote came from without looking it up.
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