We have three huge matchups today for the first round of the Tournament of Awkwardness. The voting for these matchups and the first two matchups will remain open until this Sunday at 1:00 pm CST.
Chelsea says: “Sadly, this isn’t even the worst, but my mom wouldn’t let me use those photos. (They were that bad.)”
Laura says: “I don’t know what’s worse — my glasses or that my outfit looks like a really bad wallpaper pattern.”
Caitlin (the one in the blue shirt) says: “When I was ten, I found out the digits “4T” on the tag of my jeans meant they were pants for toddlers, not capri pants for fourth graders. I was a beanpole with a bad haircut and buck teeth. I’m pretty sure this was my eleventh birthday. My little brother did his best to upstage me, but I always found a way to make a bigger ass of myself.”
Chris (Kelli’s husband) says: “She was in 5th grade and I try to talk her into that haircut every time she goes to the salon. ”
John is on the right. He says, “I’m not sure who is more awkward, me or my father. I think the Velcro sneakers, the homemade vest, and the hat speak volumes.”
Sarah has my favorite comment of all submissions:
“Overlook the shirt, which is (a) home-made, (b) buttoned wrong, and (c) printed with an island tropic pattern undoubtedly designed by someone on acid.
Overlook the weird scabbed buboes on my face, which (a) are from chicken pox, and (b) happened just in time for picture day.
Overlook the haircut, which (a) was ironically the only professional haircut of my childhood, and (b) was such an epic monument to badness that my family still refers to it as a definitive proper noun: The Haircut.
Overlook the fact that the photographer cropped the top of my head off; perhaps out of pity for the remainder of The Haircut.
Overlook the expression on my face, the only expression I made in pictures from 1988 – 1995, which says nothing if not “My level of embarrassment is causing me physical pain.”
Overlook all of that. But please don’t overlook the nice background, because it is the only redeeming part of this photo.”