The Tournament of Awkwardness

I think that 99% of all people go through at least one extremely awkward phase in their life. For most of us, it’s a bell curve: You start off really cute as a little kid, you accelerate into full-on awkwardness in middle school, and then you grow into your body and your style in high school and college. All is well.

But let’s not forget the glory of those awkward years. Let’s not forget puberty. Let’s not forget this:


Yes, these are my middle-school ID cards. I found them in a drawer when I was home for Christmas. Please fixate not just on the sleekly combed hair in 6th grade, the silk shirt in 7th grade, and the Neck and the sweater vest in 8th grade. And these weren’t photos take on random days of me wearing random outfits: these were the outfits I chose for my student ID photo sessions.

These aren’t even my best photos. I’m saving those for the tournament.

The Tournament of Awkwardness. (somewhere, trumpets blare)

Last year I created a Tournament of Cuteness on the blog, and it was a blast. Check it out if you don’t know what it is. This year I’m pretty much doing the opposite–instead of celebrating cuteness, I want to celebrate our awkwardness.

Now, you may be asking, “Why would I let you post a photo of me at the most awkward and vulnerable time of my life, a photo that hundreds of strangers will see and vote on?”

Good question. Here’s why:

  1. Although the contest is free to enter, I will be putting up a cash prize equal to the number of contestants. I will also be matching that prize for a charity of the winning contestant’s choice. So if Jane P of Omaha wins the contest out of 400 total competitors, she’ll win $400 and I’ll give an additional $400 to Jane’s favorite charity. Thus I’m hoping there is an incentive for you to not only enter the contest yourself, but also get your friends to enter, as the prize pool gets bigger for each additional person who enters.
  2. Self-deprecating humor is awesome. If you’re able to laugh at yourself, you can do anything.
  3. You will have the satisfaction of bringing joy to hundreds of people. You’ll be the Santa Claus of awkwardness.
  4. I’m happy to link to your blog, Twitter, or Facebook page in case you’d like some free publicity. The further you go in the competition (it’s tournament-style, single elimination), the more publicity you’ll get.

Got it? Here are the rules:

  1. Submissions are due on Sunday, February 12 at noon. Send one photo (any photo–it doesn’t have to be a school photo. Candid photos are fine too) to with the subject line “Tournament of Awkwardness.”
  2. You may only submit yourself to the contest. If your sibling or parent or best friend was way more awkward than you, get them to submit directly to me.
  3. One photo per person. Don’t send me 5 photos and tell me to choose.
  4. You may include a caption or description of that awkward time in your life. I’ll label photos with your first name, last initial, and age at the time the photo was taken (if you give me that information).
  5. You may solicit votes from friends or family, but preferably you’ll ask them to vote for the most awkward photo. They shouldn’t necessarily vote for you just because they know you. And please don’t cheat. Someone tried to cheat in the previous tournament, and I can tell when it happens. Just vote once.
Also, it’s very easy to snap a photo of an old photo with your smart phone. I’d recommend doing that. You might even already have such a photo up on your Facebook timeline.

Now, I understand that this tournament may end up being a total dud. I’m happy to embarrass myself in front of the world, but perhaps most people will choose not to. So if I only get a few submissions, I promise that I’ll still post them on a blog entry in a few weeks.

So that’s it! I look forward to seeing everyone at their most awkward.

18 thoughts on “The Tournament of Awkwardness”

  1. Fantastic! The hardest thing is going to be choosing just one photo! (The second hardest thing is going to be getting at least one of my parents to rifle through old photos and then admit how awkward their son was, then send something to me saying, “Hey, we think you were really awkward at this point.”)

    • Yep, I figured that most people might need to ask their parents for help. I wonder if our parents realized how awkward we were.

      • My dad will have no problem finding the picture I’m thinking of. I asked him to destroy them but he insisted on keeping at least one for memory sake.

        My caption will say, “Really, mom?” I’ve asked her numerous times why she let me get those glasses and she tells me it was the style back then. I’m embarrassed thinking about it. 🙂

    • I go from lookly like a spritely elf in ’93 to a pubescent cave troll in ’95.

      Are you going to enter the tournament?

  2. Oh, cheeks hurts from laughing. 😀 Car’s right. You were so cute! I don’t have many awkward photos, but I do have one that I don’t like from high school.

  3. In the interest of fairness, I will not post any picture from the summer I grew nine inches, also known as The Big White Shoes Era.

  4. Hubby and I are def submitting. I was in jr. high during the period of batwing sweaters and feathered bangs and my hubs was a skinny strawberry blond kid who used to break dance. LET THE GAMES BEGIN!!!


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