Tournament of Awkwardness Elite Eight: Part 2

Today we have our final two matchups in the second round of the Tournament of Awkwardness. These four are the winners of the matchups in the second and third days of the tournament. A quick refresher on the basic rules before I move on to today’s two polls:

  • You can only vote once
  • You may campaign for people to vote (but encourage them to vote for the most awkward person, not necessarily you)
  • Judge their former awkwardness compared to their current non-awkwardness
  • The winner of the tournament will receive $25 cash and $25 to give to their favorite charity
  • Polls close at 1:00 pm CST this Sunday
Sarah (before)
Sarah (after)
Josh (before)
Josh (after)
Jess (before; overalls)
Jess (after)
Jess (before; science fair)
Jess (after)

13 thoughts on “Tournament of Awkwardness Elite Eight: Part 2”

    • Thank you! I’m having fun with it too. I’m sorry you missed the deadline! Would you have a chance against these second rounders?

  1. I just want to say that my favorite part of this tournament so far is that Josh chose that “after” photo to show how much less awkward he is now compared to young Josh. I’m not even sure that young Josh would beat adult Josh in a head-to-head awkward showdown based on that photo! Classic, Josh. Well played.

    • But I’m standing in front of The World’s Largest Frying Pan! It’s not just a really big frying pan, it’s LITERALLY the largest in the world. If that’s not cool, I guess I don’t know what is.

      • yea, it would have been totally awkward if you had been standing beside the world’s third largest frying pan, but this way its pretty awesome

        • I actually think it might be MORE cool, in a novelty, hipster kind of way, if it were the third largest frying pan that you were so ecstatically standing in front of.

  2. Josh, Did you think that you were in the “awkward then/awkward now” contest? FYI your dad’s comment upon viewing these photos was “That’s my boy!”

  3. I somehow KNEW I was going to get matched against the other Jess. Man. I wimped out and submitted a photo that could, from a certain perspective, still be considered cute . Ah – it’s gonna cost me…

    • If it makes you feel any better, think of it as an act of charity: a kind deed for a poor little, awkward nerd whose only real ray of hope in life was the opportunity to someday win a contest on the internet.

      • I had that same over-sized button down and tie. The ensemble was topped off with 80s leggings in a wild print pattern. We both could have been contestants on “What Not to Wear.”


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