My Embarrassing Moments

My Embarrassing Moments

A shared journal of embarrassing pictures and stories from our awkward childhood to the present.


Pillory

Posted On Sunday December 16, 2007 By Victoria Williams

I should never have made that bet. Feeling cocky about my extensive knowledge of sports, I bet my wife that our beloved hockey team, the Toronto Maple Leafs, would earn a place in last year’s playoffs. They didn’t, much to my surprise — and my wife’s delight. We often bet on things, and this time her twisted sense of humor got the better of me. First, I was ordered to go to the local Goodwill and buy a week’s worth of women’s clothes. Seven complete outfits were required — 4 dresses, 3 skirts and blouses, plus some bras, panties, pantyhose, heels, and nightgowns. Next, I was to construct a pillory in the backyard. From the photo, you can see what happened next: I was dressed each day in one of my new outfits and made to stand in this old-fashioned punishment device for four hours. Pictures were taken to document my wife’s “superiority”. Fortunately I too have a sense of humor, and I must confess that, despite the long hours in the pillory, living as a woman for a week was a lot of fun.

Rate This Embarrassment: 7.3/10 (32 votes cast)
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The 'game'

Posted On Wednesday December 12, 2007 By Natt

well i think i really like this guy so i flirt alot and make it obouis and he knows that too but when i ask him out he ses no cos we always pull pranks on each other then i get embarrased and say good cos that was a prank no offence ur not my type which gets me angry cos i can never really ask him out i say its a prank cos itd be awkward if it wasnt.

Rate This Embarrassment: 3.3/10 (47 votes cast)
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Track Meet

Posted On Friday December 7, 2007 By Amy

Back in 8th grade 2 years ago I was on the track team and our team was in charge of the regional meet. Our coach, who was totally hot, put me on the “hurdle crew”, because I wasn’t running at that meet. At the school that the meet was at, there was a set of bleachers inside the track so when runners got to the curve you couldnt see them anymore. They were about to do the 300 hurdles, so we all started moving our hurdles onto the track. I guess they had to do another race or something, and the guy said over the intercom “hurdle crew please remove your hurdles” I wasnt paying attention so I kept putting hurdles out, so did the guy right after me who was behind the bleachers where nobody in the whole world could see him. They said over the intercom “the lady on the curve please remove your hurdles”, which was me, I kept puttin them out not paying attention, they said it again “the lady on the curve please remove your hurdles” there was like hundreds of people there all watching me look like a idiot and I didn’t even notice, the guy after me was doing the same thing, but nobody noticed, and by that time all my teammates were yelling at me, but I wasnt paying attention, till finally after they had to say it on the intercom 5 times I heard and removed my hurdles. I got a few stares the rest of the night.

Tags: embarrassing, hot, hurdles, meet, sports, track

Rate This Embarrassment: 6.1/10 (29 votes cast)
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