Tournament of Awkwardness Final Four: Part 2

Today’s matchup between Sarah and Jess to decide who goes to the finale and who shuffles home is of epic proportions. I’ll let the contestants speak for themselves below their photos; for now, here are the rules:

  • 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 awkwardness not only by their photo, but also by their story
  • Polls close at 1:00 pm CST this THURSDAY
Sarah's red bathrobe incident

Sarah says, “This picture [right] was taken at 7:30am before I went to school on the last day of 8th grade. Despite the fact that my orthodontist had recently offered me headgear, and despite wearing a training bra just for looks rather than by necessity, I believed my awkward days might be coming to a close. That belief was premature.

There had been an 8th grade class memo that “students should dress up for the last day of school.” It was only after classes started that day that I realized, suddenly, painfully, irreversibly, that when they said “dress up” they had meant “dress nicely.”

I spent the whole day wearing this; unable to go home and change because my parents weren’t there; unable to hide in the bathroom for fear someone would recognize the distinctive knee socks underneath the stall door. The Red Bathrobe Incident haunts me still. ”


Jess says, “Please accept this journal entry from 14 year old Jessica as proof of my long-term, sustainable awkwardness. It was pervasive, I assure you. I am extremely invested in this journal entry going public, because I think it’s hilarious.

Tonight I went to a movie: WITH BOYS! Okay so I go to the movie fifteen minutes early and no one was there yet (ERG! DAD!) Colin came first and he was like “I’m starving, wanna come to the food court with me?” HE got pizza and I had to sit there for like, forever, watching him eat. It was totally silent. I felt like such an idiot. When he was finished, we couldn’t find anyone else and the movie was starting. Colin’s cool but it was just him and me, and I was totally hyperventilating. He’s a lot shorter than me and I kept thinking people were staring. Anyway, then Pat and Hayden walked in and I scootched over so they could sit by Colin. Now I was sitting by Hayden. He was like “Omg did I take your seat?” and I was like “It’s fine!” and I was shaking. Levi and Nick finally came back, and Nick went to get a pop and Levi sat by me. They said that all the girls were going to Evolution instead, and I was like “WHAT!?” but I didn’t say anything. At that point, I had ripped my ticket into little shreds. LoL. Then we went to dinner and a lot of funny stuff happened. I sat by guys again, and I wasn’t nervous!!!! I know!!!! And then afterwards, it was like 10:30 and we were waiting for rides and I was like totally comfortable.”

14 thoughts on “Tournament of Awkwardness Final Four: Part 2”

  1. Here’s runner-up Josh’s awkward story:

    The year was 1995. I was a freshman at a new high school full of people just as awkward as me and science had finally advanced far enough to allow me to trade my giant glasses for contacts. Life was good.

    About halfway through that school year, a group of sophomores invited me to a surprise party for, Ben, one of our friends. I was stoked. A real high school party! And these were sophomores! Surely an evening of classy tuxedo clad hijinks and shenanigans were in store.

    The evening of the party arrived. My mom dropped me off and I confidently stepped onto the front porch and rang the doorbell. Ben’s brother answered.

    “Hey, where is everyone?” I asked.

    “Um, you know the party’s tomorrow, right?”

    F-word. No, sadly, I was not aware of this critical factoid. Apparently in my excitement, I had gotten the date for the party wrong. The surprise party. And now I was on the doorstep of ruining the surprise and (I assumed) my life. This was bad. And really really awkward.

    Luckily, Ben was as at soccer practice and not home yet. His mother offered to give me a ride, which I had no choice but to accept. I spent the ride in silence, crouched down near the floorboard in hiding just in case we should pass Ben and his father on the way. It was awful.

    I spent the rest of that night at home feeling a level of embarrassment that only a 14 year old can know. The next evening, I went to the party, the actual party, where I was for some reason the main topic of conversation.

  2. And here’s runner-up Jess’s awkward story:

    My awkward stage started around age 8 and continued well into high school. 9-13 was particularly brutal. Most of the awkwardness stemmed from my complete lack of fashion sense. The era consisted of owl glasses, oversize sweaters/sweatshirts/shirts occasionally accompanied with print pants and/or ties, and only a passing acquaintance with a hair brush. As to specific incidents during this time – two come to mind. The first was when one of the guys in my 6th grade gym class asked me out as a joke in front of the rest of my peers. The second – which may make for a slightly less depressing antidote – involved my refusal to acknowledge that I was going through puberty. I come from a long line of at least reasonably endowed German women. When my body started to fulfill my genetic heritage around age 12 however, I tried to ignore it. Despite their total inadequacy, I stubbornly continued to wear “training bras.” One day during a game of volleyball I came to fully appreciate how poor a decision this was. While jumping to set the ball, my bra completely snapped. NOT something a girl wants to have happen in junior high.

    • I can relate to this story…except mine was in high school (rival basketball game) and involved a bra that fastened in the front. I haven’t worn a bra like that since the incident. Probably never will. 🙂

      • Laura–I, and every other man, support your decision to not wear front-clasp bras. Many a man has been driven mad trying to find the clasp in the back of a front-clasp bra.

        • I call shenanigans. I enjoy a front clasp bra, for the dramatic action of presentation. Not as much the clasp, but the welcoming reveal. Like someone ceremoniously opened a set of double doors to invite you in to a grand ballroom.

          • Red–Perhaps you’re thinking of the infamous front-clasping red swimsuit in Fast Times at Ridgemont High? I’m in full support of front-clasp swimsuits in that fashion. I put them in a different category than bras, as I don’t think I’ve ever had to unclasp someone’s swimsuit.

      • I had a front clasp bra break in a separate incident while clothes shopping with my mother. Another very embaressing situation. I swore off them for over a decade, but eventually tried them again. And I love them. What I’ve learned is that you really, really don’t want to buy a cheap front-close bra. Plastic gives up the ghost too easily.

  3. If only this could be the finals! I thought science fair Jess was a certain winner from the beginning (I have, in fact, seen her wearing a beard just for fun…disturbingly recently, in fact, and not on Halloween), but Sarah saved the big guns for the last fight! That red bathrobe debacle is not only hilarious, but probably the most embarrassing thing ever.

  4. I admit, I thought I was shoe-in. This defeat is going to be difficult to take gracefully. In large part because this is a tournament of awkwardness.


Leave a Reply

Discover more from

Subscribe now to keep reading and get access to the full archive.

Continue reading