Congratulations to all the winners of Lizzie Post‘s book How Do You Work This Life Thing. We got overwhelming response, but we could only chose the best, most embarrassing moments as our winners. Boy, did we have some doozies!
Here are some of our favorites…
Graduating college, mom came up to help pack and move. So, I did some pre-packing of my own, hididng things that were not appropriate for “mom’s eyes.” Several months later, back in my hometown, I decided to take up Pilates. So, first class ever, throw on my old gym shoes and saunter in. Who knew you didn’t wear shoes? So I kick them off and seat myself on the mat. A few minutes later, with my butt up in the air and my feet over my head I start to hear snickering. I mean, I know my butt is big, but c’mon, thats why I was in the class. When I finally put my rear back down, I look at my mat and low and behold, a condom (still in its wrapper) is sitting right there in front of me (in clear view while my butt was up in the air).
Obviously I had thought it a good idea to throw the thing deep in the tennis shoe so mom wouldn’t find out, only to have it reappear months later when I wore the shoes again and it fell out on my pilates mat. 2 options, act
totally offended that someone would put a condom on my mat and make a scene, or (the option I chose) discreetly shove it under my mat and hope the hot guy two rows back didn’t notice. Pilates was clearly not the class for me and my condoms, I did not return the following week.
I was visiting a male friend I had made in England while I was on vacation. He and I had been emailing and chatting for months and were going on a trip and spending a few days together while I was over. We ended up sharing a bed for a few nights and one morning we ended up making love, or attempting to. I had been so dehydrated on the 3-week vacation because it was summer, super hot and I just wasn’t spending my savings on bottled water, so in the midst of our passion, right when I was about to climax, I got a charley horse in my calf. I mean right when I was about to… I started flailing about in the bed and yelling, and not in the sexy, passionate way either.
If that’s not bad enough, he patiently spent another ten minutes or so getting me back there, and as soon as I was about to climax again, you guessed it. Another charley horse. More flailing and yelling and sitting up in bed grabbing my calf and bouncing around trying to get it to stop.
Needless to say we gave up after that. We never tried again, and now he’s got a girlfriend, so I blame it on the charley horse. I have never been more mortified.
More cringe-worthy stories sent in by readers after the jump.
I had just taken a highly sought-after job as an assistant at a major movie studio in L.A. After a few weeks of working there, I was at a lunch where the President of Production was present… the kind of lunch you’re just honored to be included in. When things were wrapping up I decided it would be a good time to do some quality ass-kissing and asked how his 7-year-old daughter’s soccer game had gone the evening before. He said “fine” and rushed me off in the typical exec fashion. But I wasn’t going give up without at least a decent dialog taking place. I recounted to him how I had passionately played soccer in my younger years, but had stopped when my nose was
shattered by a ball traveling at lightning speed. He nodded… saying “oh yeah… those injuries are the kind you never forget”. Enthused that he was finally engaged in the conversation, I turned the focus back to his daughter so as not to seem self-involved, and asking him, “So… has that ever happened to her.?” A pause… clarifying… “Has
she ever taken any balls to the face?”
It was about 2 seconds later that I realized, while I know and he knows we’re talking about sports… the image I had just put in his head is not one which any parent ever wants to have. Things were awkward between us until I left the job over a year later.
I’m a gay guy, and I seduced my boss. On our very first night together, we were pretty drunk and I took off my shirt and threw it over the lamp in the living room to “set the mood”. So, it’s the middle of the night and I get thirsty, so I pop out of the bed, stark naked, and rather, um, aroused, and go into the kitchen for a beer. At that very moment, my forgotten, smoldering shirt on the lamp sets off the smoke detector. My female roommate, startled from deep sleep by the sound of the smoke detector, barreled from her bedroom, is momentarily shocked to see me standing naked in the kitchen, and then runs out the doorway and into the street, butt naked.
Check out the Books Forum at Famesters to read more like this, and get the opportunity to tell us what your most embarrassing moment is! P.S. Feel free to register on Famesters and join the the conversation.