Let the Tournament of Awkwardness Begin!

When I announced the Tournament of Awkwardness two weeks ago, I wasn’t quite sure what to expect. It’s a lot to ask people to submit photos of years that they might like to forget, years filled with braces and odd clothing, with devastating hair styles and androgyny (there are at least three entries where a “Guess the Gender” game would result in a 50/50 male/female split).

Plus, unlike cute photos of our pets and babies, we don’t carry around photos of ourselves from middle school in our iPhones. It took some work for people to procure these photos.

The work was well worth it. To the 18 entrants in the tournament, thank you for sacrificing time and dignity for the sake of some good times on the blog. I said the prize money would be double that of the number of submissions (half for the winner, half for their charity of choice), but I’m going to make the prize money a nice, even $50. That’s $25 for the winner, $25 for their favorite charity.

I’ll post two matchups a day this week, with all polls for the first round closing this Sunday at 1:00 CST. I’m curious to see if people will petition votes or if the last thing they want is for their friends to see these photos. We’ll see.

The matchups were determined randomly. Here are the first two, the winners of which will face each other in the second round:


Anna writes: “No one was as awful as me…during my punk phase…which coincided with acne and braces. Boom. Age: 13 or 14. Sex: female (despite appearances to the contrary).”



Jasmin writes: “It was photo day of my senior year. I was not ready for the photo day. I was a mess in the brain. I never got the fashion trend or hair dos or don’ts, so yeah…. not the best photo from high school.”


Kendall writes: “It’s my freshman year of high school in the color guard. I was 14.”