Tournament of Awkwardness Elite Eight: Part 1

For those of you who participated in the first round of the Tournament of Awkwardness, thank you so much for your wonderfully awkward photos and stories. They will be treasured forever by random people who stumble upon this blog.

Now, on to Round 2! Eight contestants remain in the hunt for the cash and the dubious distinction of being the most awkward.

Awkwardness is about much more than a single bad photo day. Awkwardness is an unwitting lifestyle choice: the clothes, the social naivete, the way you viewed the world.

A few clever commenters suggested that they see what the contestants look like now so they can use the comparison to gauge the relative degree of awkwardness–the before and after. After all, as far as my readers know, these people are still just as awkward as they were in middle school. Fortunately, all eight of the remaining contestants provided me with current photos, as well as awkward stories (which I’m saving for the next round).

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)
  • Polls close at 1:00 pm CST this Sunday

Today’s matchups come from the first and second days of the tournament. Remember, you’re judging their former awkwardness compared to their current non-awkwardness.

Anna (before)
Anna (after)
Kendall (before)
Kendall (after)
Chelsea (before)
Chelsea (after; on the left)
Caitlin (before; blue shirt)
Caitlin (after)

8 thoughts on “Tournament of Awkwardness Elite Eight: Part 1”

  1. Well, it appears my inability to think of anything clever to say around attractive women extends to the online world. Given that my usual fallback when tongue tied by a lass (performing a feat of strength) is impossible via computer, I’ve got nothing.

    Chelsea, there is a 4% chance I demonstrated my inability to be funny around women and my great strength to you one night. If so, I apologize. I don’t know why I thought it would be a good idea to pretend I was a vampire. I knew lifting that table was a bad idea when I did it. I’m sorry. I really am. Please take it as a compliment that I tried.

  2. Oh! Everyone turned out so preeeeeetttty!!! I love a happy ending!

    I am sort of shocked by the results of the Anna vs Kendall match-up so far, though. (I’m also shocked by Brad’s assumption that claiming to be a vampire is a viable pick-up line…but I digress.)

    Kendall was always a good looking girl. In that picture, she’s clear-skinned, well-groomed, and probably had bathed recently. Her only mistake was joining the marching band, which was a cruelly thankless master that dressed her in a size XXL disco ball with sleeves. You can see her clenching her fists at the injustice of it all.

    Anna, on the other hand, is a different story. Unless there was a No-Bathe Marching Band of Choker-Wearing Jaded Teens, she had no one to blame but herself.

  3. Sarah, to be clear, one of my friends had just killed a bat that was flying around the house. One of them would later waterboard himself. It was a weird situation. I was just trying to keep up, but apparently modern vampires are not created via bat bite. That’s why Chelsea (?) didn’t appreciate my humor, or so I tell myself.

    Frankly, I’ve gone with things waaaayyyy stranger than that in vain attempts to impress the fairer sex. I once pretended to be a ghost. I learned to recite an impressively long part of pi. I played Mike Tyson’s Punchout with my eyes closed. I sang lead in a three man band whose only song was “Michael, Row Your Boat Ashore”. And that’s not even including anything I did during my Kate the Med Nurse phase.

    The vampire thing was actually pretty funny, if you ask me. You know what? I take back my apology. It was awesome. Chelsea, you missed out.

  4. I’m with Sarah, I think these people consider themselves awkward in their adolescent photos because they ended up too beautiful for words as adults.

  5. I still can’t believe that Caitlin is the blue shirt one. And how impressively un-awkward the blond girl in the white shirt behind her is! I mean, that’s impressive. That girl’s mother must have owned hair products… unlike mine. Oh my. 5th grade. Oy. Umbros and plain purple shirt = bad call every time.

  6. I was a total wreck before I hit puberty and discovered orthodontia. See, boys? This is why you shouldn’t discount the dorky girls. Give geeks a chance! Oh, and the girl behind me is STILL impressively un-awkward; it’s completely unfair.


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