Tournament of Awkwardness Final Four: Part 1

After an elite eight that revealed how amazingly unawkward the contestants are now (see here and here), we have some new awkward stories to accompany the old photos today. I had asked for these stories from the full Top 8, so that means there are four stories that won’t make it into this post. I’ll post two of those stories in each of the comment sections of the the two Final Four posts that I write.

  • 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

Kendall’s awkward story:

As awesome as this color guard uniform was, it came with a burden to bear. As I waited to run onto the field that first night, I saw that the bright lights of a Friday night football game were like an x-ray to white spandex stirrup pants. My polka dot underpants were shining through.

Surely, it was just because I was so close. No one else could see, right? I had no choice but to go on and find out. I was so distracted though that at a key point in the performance, I dropped my wooden rifle. Onto my face.

I learned from my mother later that night that distance did not hurt the x-ray effects. Apparently the whole stadium could see my polka dots too. Oh well. I hope they enjoyed the show.

The next day, my mother and I went to find white pants to wear underneath my uniform. I don’t know which is more awkward – showing a few thousand people your underwear while wearing a sequined jacket, or having to special order white spandex pants from a sporting goods store with your mother.

Caitlin (blue shirt)

Caitlin’s awkward story:

Braces, puberty, an epiphany (long hair makes me look like a girl!), and a hot Marine made a world of difference on the outside. I may not look as awkward, but I’m just as dorky now as I was back then.

It’s so hard to single out one instance of awkwardness that’s more embarrassing than any other. Everyone called me sir or handsome, I had no coordination or athletic ability whatsoever, and I developed a flair for the dramatic that made me the center of attention (never in a good way) throughout elementary school.

In sixth grade, the boy I had a mad crush on asked me to be his girlfriend. I didn’t get all stupid and giggly; I managed to keep my composure. I simply introduced him to Junior (the Cabbage Patch baby I’d spent the last few years raising as his love child) and began asking him typical grade-school sweetheart questions like “should we have our wedding indoors or out?” and “how many more children should we have?”. It took him approximately eight minutes to break down and admit the whole thing was a joke (I had my first mortal enemy that year and she was diabolical) and he never liked me. AT ALL. He asked the teacher to move his seat and he never spoke to me again. I continued to raise Junior on my own until high school, when my mom sold him at a yard sale. It’s all very tragic really. Kids can be so cruel.

26 thoughts on “Tournament of Awkwardness Final Four: Part 1”

  1. Runner-up Anna’s awkward story:

    It was first grade, I was taking the annual required CAT test, and I had to pee – urgently. Completely unable to think of anything other than the unrelenting pressure in my bladder, I gazed anxiously around the room at my classmates as they scribbled away diligently. Finally, my pride gave way. Sweating, I approached my teacher and asked if I could please use the restroom. Gently, she reminded me that there was no walking in the hallways around during test time; I would have to wait. I had embarrassed myself enough by asking, and begging was out of the question, so I returned to my seat and focused on furiously crossing my legs. It wasn’t enough. In mute horror, I felt my body reject my furious commands. It was all I could do not to break down and cry I felt the warm release, but instead my survival instincts kicked in and I calmly, slowly, took off my sweater, wriggled it under my moist behind, and tied it around my waist. Step one: complete; but what to do about the small puddle under my chair? Suddenly, I heard my teacher’s voice. My blood turned to ice as she said, “Anna, oh no!” Time froze. My heart pounded. “Your juice spilled!” I risked a glance downwards – somehow, miraculously, my waterbottle full of juice had happened to fall to its side, masking the true nature of the surrounding liquid. Fate was on my side that day. My classmate Tommy helped me clean up the “juice,” another classmate admired my stylish sweater-around-the-waist look, and I was home free.

    Runner-up Chelsea’s awkward story:

    There are so many embarrassing stories to choose from. How bout this- I switched schools in middle school. So the first day of 6th grade, I didn’t really know anyone, and I was chubby and shy and awkward, and it was rough. The “cool girls” had already decided that I wasn’t one of them (surprise, surprise). The school had a bunch of stairs outside that led up to the main entrance. My backpack was super heavy because I had ALL my books in it for class. At the end of the day, I go outside and start walking down these stairs and my backpack is so heavy that it literally tips me over. I rolled down these stairs (probably a good ten!) in front of everyone, my first day at a new school. Needless to say, EVERYONE was laughing at me.

    • I can relate to Chelsea’s story. I once had a super heavy book bag like hers. I was walking home with my uncle and some kid ran past and nudge me off my balance. Down I went, flipped over like a turtle and couldn’t get back up. I tried a couple of times to try to stand back up on my feet. My uncle pointed and laughed at me with everyone else. I finally figured out how to release myself from my armor book bag, stood up, and let my uncle to carry it for me.

      Now the thing on my mind is points, points, POINTS! I wish I can redeem them for a pumpkin muffie like at Panera.

      • I think the best part of your story, Jasmin, is your uncle’s reaction and unwillingness to help. I hope he’s redeemed himself since then.

  2. Kendall,

    I didn’t think it was possible, but you have a shot at defeating Tie Jess next round. And take it from me, discussing underwear mishaps with your mother is more awkward than anything else you could possibly encounter.

    • In other words, you’re already assuming that Necktie Jess is going to destroy me in the other match-up of the semifinals, so you’ve jumped ahead to pitting Kendall against her in the next round? You definitely underestimate the homemade-clothes-wearing, pants-wetting, glasses-and-braces-wearing, guy-repelling, delayed-pubescent, social retardedness of my younger years. By younger years, I might mean ages 0 to 25.

      *But I do agree that Kendall’s story is laugh out loud awesome awkwardness. I had been a devoted Caitlin voter until I read it, and have now joined Team DiscoBall.*

      • Sarah and Brad–I’m glad you all are taking the stories into account when you vote. I wanted this to be about more than an awkward photo. That said, as awkward as Necktie Jess is, Sarah has a great story that I’ll be posting today. Wait for it.

  3. Also, I’m a little concerned. Everyone’s awkwardness seems to be long in the past. Does anyone have a recent story? Please say you do. Then I would feel better about posing for a picture last week with a 14 foot python wrapped around me in an ultimately futile attempt to impress a lady.

    • Recent story for you B-Rad:

      This one actually ties in well with the whole falling down the stairs fiasco mentioned above. To preface this story, I went to an admittedly hifalutin smaller private southern college. As a junior in college, one of the biggest things that the women looked forward to was called ring dance–it was our version of a debutant ball. Fathers officially took their daughters and dates were more like arm candy. (Sidenote: I was sort of like the circus peanuts of arm candy.) Anyway, I managed to break a small bone in my foot a day or two before the ball (which is a worthwhile story in its own right) and my date, who was a friend, was nice enough not to uninvite me even though I couldn’t dance. Her father was a licensed acupuncturist and plied his trade on my foot in an attempt to allow me to actually dance rather than hopping around on crutches. While I thought the acupuncture made for an interesting story, I’m unsure if it helped (but grateful for the attempt). Needless to say, I was still on crutches the night of the dance. The night was going well until I attempted to climb a grand staircase with crutches and one slick-bottomed tux rental shoe. I made it about halfway up before completely slipping, throwing one crutch into the crowd, and bouncing unceremoniously down the rest of the stairs. Luckily, the only additional injuries were my armpit (due to the one crutch I still clung to) and my pride. It was a “music stops, everyone stares” type of moment.

      • “The circus peanuts of arm candy” is an awesome line. Perhaps autobiography-title worthy?

        I think I’ve heard this story before, but I still laughed out loud (at work) when I read, “throwing one crutch into the crowd, and bouncing unceremoniously down the stairs.” Is there a way to ceremoniously bounce down the stairs? I’d like to see that.

    • Recent shame:

      After the childhood trauma of The Haircut, I grew my hair out all the way through high school. At the end of my senior year, I braved a trip to the salon hoping for something that would make me cute for college.
      “Maybe a shoulder-length bob?” I said.
      “I have a better plan,” the stylist sneered and plunged the scissors toward my hair without further discussion. Within the next second, I watched in mute horror as she cut off 15 inches of hair and gave me something related to a buzz cut mullet. From a combination of shyness and shock, I didn’t say anything to stop her.

      I worked at Taco Bell that summer, where we wore only the finest in gender-bender unisex uniforms. People would call me “sir” and “young man” all the time to get my attention at the counter. Maybe they wondered why that young man with the buzz cut mullet looked a bit femme and was named Sarah, but they never corrected their mistake. Out of total estrogen insecurity, I started wearing a ton of make-up: think of Mimi from the Drew Carey Show.

      One day, two sweet old ladies came in. One said “Excuse me young man,” then actually gasped out loud when I turned around wearing all that make-up. The other one huffed something that sounded like “Abomination!” then they both walked out. As they were leaving, I heard one of them say to the other “I didn’t know they would hire one of those cross-dressing transvestite men in a place like this.”

      • I seriously need to stop reading these at work. Amazing, Sarah. Amazing. Although keep in mind that if you make it to the finale, you’ll be asked to state your case for Most Awkward, so hopefully you have some other material for that.

        The word “sneered” was a particularly nice addition.

  4. Kendall- I understand all too well the shame of the awkward color guard uniform, though the disco ball look is a lot more extreme than the maroon lycra and rhinestone number we had at my school. I fondly remember thinking that we were pretty hot stuff back then.

    Brad- A recent story for you (and it’s related to Kendall’s story) is a few weeks ago at the wonderful gym, I didnt realize that I accidentally brought regular leggings (normally worn under dresses) instead of my normal workout pants. At the time, I didn’t think anyone would notice, as they were just a shinier version of my normal gym attire. It wasn’t until I walked back into the locker room for my bag to head home that I happened to look in the mirror and see that my hot pink and white polka dot panties were completely visible through the black material. Since that day, I now make a point to double and triple check my gym bag before leaving home. 🙂

  5. Seriously, voting public. Everyone has worn a sequin-adorned top at some point in our lives–this is not all THAT unusual. Despite the underwear snafu, Kendall really does look like a pretty normal kid.

    Look at Caitlin’s face. She consciously made that ridiculous slack-jawed face, wore a haircut like a toupee I once found in an uncle’s drawer, and…are those zippers at the bottom of her toddler-sized pants??? It will be a tragedy if this picture does not make the finals.

    • I believe those are zippers, Trev. Caitlin originally said this about those pants: ““When I was ten, I found out the digits “4T” on the tag of my jeans meant they were pants for toddlers, not capri pants for fourth graders.” A common mistake. I’m pretty sure I’ve pulled a Michael Scott and accidentally wore women’s clothes thinking they were for men.

    • T-Mac, you have to be kidding me! You cannot be serious!

      Caitlin looks like a perfectly normal little boy that is just playing with his food. Yes, her (his) arm is a little lanky, but her dress is perfectly normal. I mean, its a blue t-shirt and jeans (and who of us didn’t wear those thick socks?). The fact that that cute little blonde girl in the white shirt allowed a picture of her to be taken in the presences of Caitlin proves that Caitlin could not have been that awkward. If there is one truth that holds through time it is that cute, blonde, middle school girls do not hang out in the basement with awkward girl-boys. If anyone in that photo is awkward its the ghost that appears in the foreground, but that’s not who we are voting for.

      Now, as for Kendall: note that rigid stance. Note those hands, clinched into fists, that are screaming “I DON’T KNOW WHAT TO DO WITH MYSELF RIGHT NOW.” Note the height to which the pants are pulled. Note the collar that cannot be un-“popped.” Note the far away gaze in her eyes that is a mixture of equal parts pride and shame. Note the bangs, T-mac, note the bangs!

      Even without the underwear story Kendall is the runaway winner here. But when you add the underwear story–the AGONIZING underwear story–this girl cannot be beaten. Not only did she expose her underwear to a crowd of high schoolers (an all their siblings). Not only were they polka dot. Not only did she realize, in real time, that this exposure was taking place (oh! to have been blissfully unaware!). Not only did she smack herself in the face with a fake, wooden rifle. But she had to go to her mother, on the night of what should have been her triumphant color guarding debut, and say the words “mother, did you and several thousand other people see my polka dot underwear shining through my white pants as that wooden rifle slammed down into my face?” and she had to sit across from her mother and hear the words “yes, honey, we did. We did see your polka dot underwear, but its ok because we are going to go together and special order some white spandex pants for you at the local sporting good store.” This did not make it ok, T-mac. You know that this did not make it ok. Only 15 years and a cathartic confession on can make this ok.

      Kendall literally defined awkwardness in this photo and anyone who votes for the normal girl with the boy cut is not recognizing the full extent of awkwardness.

      The were polka dot, T-mac, they were polka dot!

      • The cute little blonde girl in the white shirt was a pathologically shy little thing who lived across the street from me and we were not middle school kids in a basement but 5th graders at a kitchen table. The boys at my party were my little brother (the awkward kit in the foreground) and his obnoxious friend (laughing at me from the sidelines). The blue shirt fit me like a tent (I think it was my mom’s) and my pants were hideous stonewashed jeans with zippered ankles which I wore with slouchy socks (also probably my mom’s) but I CHOSE THAT OUTFIT TO WEAR AT MY BIRTHDAY PARTY whereas Kendall was forced into her uniform. And that slack-jawed, mouth-full-of-food, gorilla-hands pose was (again) MY IDEA OF A COOL PICTURE instead of a “stand here and say cheese” yearbook photo.

        While I do think Kendall deserves sympathy votes because her mom bought her bold, polka dot underwear in high school, I would gladly have traded places with her. GLADLY. In a heartbeat. The fact is, I was a loud-mouthed train wreck with a $3 haircut and the personality of Steve Urkel. I was the kid who shoved a whole chicken nugget in my mouth after an hour of standing over the nugget pile in plastic gloves during cafeteria duty and was publicly berated by the lunch lady in front of the entire school with chipmunk cheeks full of fried poultry; “THE NUGGETS ARE FOR THE HOT-LUNCH STUDENTS! YOU SPIT THAT THING OUT!” I was the 2nd grader who forgot to wear pants to school under her snowsuit and had to spend the day making a swishy sound wherever she walked.

        No picture can properly convey the awkwardness that was.

          • No matter how I far I get in this tournament, I will never be able to top “My level of embarrassment is causing me physical pain”. I laugh every time I think about it! (I know you can’t see me right now but I’m totally kowtowing to your former awkwardness)

        • “I was the 2nd grader who forgot to wear pants to school under her snowsuit and had to spend the day making a swishy sound wherever she walked.”

          Out of many amazing lines in today’s comments, that might be my favorite.

      • “If anyone in that photo is awkward its the ghost that appears in the foreground, but that’s not who we are voting for.”

        I think there needs to be another Tournament of Awkwardness for the other people/creatures/animals that are in the ToA photos.


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