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.”

16 thoughts on “Let the Tournament of Awkwardness Begin!”

  1. Thank you for bringing the awkward youthfulness out in all of us. I do have one potential improvement request for next time. Only upon seeing these pictures did I realize that the level of awkwardness would be accentuated/clarified if your readers knew what each person looks like today. For example, does Orianna look roughly the same and still wear that Smurfs shirt, or did the sex change of ’02 make her look a lot more like Ricky Martin?

    • Trev–I like that idea. I think maybe I’ll do that for the final four and/or finale (along with Sarah’s idea below of including a few awkward photos for the full picture).

  2. Wow! We’re just 4 photos in and I’m already fascinated by the nuanced levels and types of awkwardness. I think it may be helpful to see more than one picture to document the extent of the awkward phase — to get a better sense of each candidate’s “body of work,” so to speak.
    Any chance we can get a full portfolio from the finalists as the end gets nearer?

    • Realize that this is a compliment, Jasmin! 🙂

      I actually did vote for you for a few reasons.

      1. I was shocked –SHOCKED– that this was your senior year photo. I would have pegged you for 14 at the oldest. That in itself made me feel bad for you, and pity is a great basis for an awkwardness vote.

      2. I loved the contrast between the meekness of your hair and glasses, but the seemingly daring neckline of your shirt. Had the photographer placed you in the frame an inch above where he did, it would have been a lot more awkward…

      • Thanks for the compliment and the vote, Katie!

        1. Yeah, I look like a youngling, but I’m not that young. There was this one time at the theater that the ticket seller said I look like 12. 12! I was 23. My heart dropped. Maybe it’s time to drop my warm puffy winter coat and wear my peacoat more often.

        2. It’s the sexy jailbait look I was going for. Yep, yep. LOL!!

  3. Anna, I feel like when you say “punk phase” that you really mean “No Doubt phase.”. I can practically see your foot tapping to “Spiderwebs” in that photo. Am I on the right track with that guess?

  4. These photos have made me realize that we’re our own worse enemies. Honestly, I see nothing wrong with them, but I would be plenty embarrassed if they were my photos (I didn’t contribute for that very reason!). I think we consider our youth/teenage years to be FAR more awkward than they actually were. Of course, I’m still not submitting my own photos…

    • Em–Definitely, I think we give ourselves a hard time. That’s why I like this tournament–it gives us a chance to look back, laugh at how silly we were, and move on.

  5. Orianna – That’s actually kind of cute, especially since you have the exact same smile as the Smurf on your shirt.

    Jasmin – Most of your problems in that picture come from looking young, a quality I’m sure you will find handy as you age.

    Kendall – I don’t know why colors need guarding, but your clinched fists make you look like you’re up for the challenge. I give you a bit of a pass because I doubt the jacket was your choice. I am a bit curious, however, as to what exactly you are looking at.

    Anna – Oh my. Anna. Anna, I’m sure you have grown up to be a lovely woman in possession of a wonderful sense of humor that this angry young lass did not have. You’re probably making a wonderful contribution to the world. But Anna, this…this is bad. And unlike Kendall, I can’t see there being an adult to lay the blame on for what’s happening on the docks here. The choker was your idea. I applaud you for your willingness to share your awkwardness for everyone’s enjoyment, but this is bad.

  6. This is a great contest… If you can get Richard Dunn to post a photo of him at the Grand Canyon at age 14 riding a donkey, it would win… hands down! 🙂

  7. Jasmin vs. Kendall is the hardest match-up thus far. I mean, it’s simply impossible. Both are excessively more awkward than Aviator Eyeglasses Josh from Day 3 of Round 1, and yet he might come out victorious due to being pitted against the adorable Katie.

    This is simply too hard!!!!! I vote for both Jasmin and Kendall. 🙁


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