Name That Gender: Round 1 Continues

We have three huge matchups today for the first round of the Tournament of Awkwardness. The voting for these matchups and the first two matchups will remain open until this Sunday at 1:00 pm CST.


Chelsea says: “Sadly, this isn’t even the worst, but my mom wouldn’t let me use those photos. (They were that bad.)”


Laura says: “I don’t know what’s worse — my glasses or that my outfit looks like a really bad wallpaper pattern.”


Caitlin (the one in the blue shirt) says: “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. I was a beanpole with a bad haircut and buck teeth. I’m pretty sure this was my eleventh birthday. My little brother did his best to upstage me, but I always found a way to make a bigger ass of myself.”


Chris (Kelli’s husband) says: “She was in 5th grade and I try to talk her into that haircut every time she goes to the salon. ”


John is on the right. He says, “I’m not sure who is more awkward, me or my father.  I think the Velcro sneakers, the homemade vest, and the hat speak volumes.”


Sarah has my favorite comment of all submissions:

“Overlook the shirt, which is (a) home-made, (b) buttoned wrong, and (c) printed with an island tropic pattern undoubtedly designed by someone on acid.

Overlook the weird scabbed buboes on my face, which (a) are from chicken pox, and (b) happened just in time for picture day.

Overlook the haircut, which (a) was ironically the only professional haircut of my childhood, and (b) was such an epic monument to badness that my family still refers to it as a definitive proper noun: The Haircut.

Overlook the fact that the photographer cropped the top of my head off; perhaps out of pity for the remainder of The Haircut.

Overlook the expression on my face, the only expression I made in pictures from 1988 – 1995, which says nothing if not “My level of embarrassment is causing me physical pain.”

Overlook all of that. But please don’t overlook the nice background, because it is the only redeeming part of this photo.”

30 thoughts on “Name That Gender: Round 1 Continues”

    • Don’t sell yourself short John, you look really awkward. I think the guy beside you would be a shoo-in. If anything its your super-cool hat and lack of feather that might do you in. Sarah just looks like a character from a production of “Oliver!” set in the south pacific. She’s actually kind of a cute little out-of-place english boy.

      • I’ll second Bryce. The Tonto to your Lone Ranger (or whatever is going on there) is so awkward even the cat is hiding. He should have been an odd side character in Office Space. Any chance you can retroactively enter him instead of yourself?

    • Egads! Are those Moon Boots, John?!
      I didn’t notice them the first time around because I was too busy perseverating on Caitlyn’s toddler pants from the previous match-up, but the longer I look at them the more I think I should campaign for votes on your behalf. The rest of your ensemble is *probably* a costume (i.e. a sign of temporary fun rather than evidence that you were a persistent social pariah), but I’m guessing those ingeniously awkward shoes were for daily wear, weren’t they?

      • Not moon boots, Velcro shoes. And not the Velcro with two strips, but the single wide Velcro strip.

        My commentary I included with my entry (and Jamey failed to include) was: “I’m not sure who is more awkward, me or my father. I think the Velcro sneakers, the homemade vest, and the hat speak volumes.”

        I like the commentary on the cat photo bomb. This cat was ahead of her time, photo bombing even before it was cool to do so.

      • Sarah, just want to tell you that you were so adorable in that picture, even though you think it’s awkward. And I really want to build a time machine and give you a hug because you looked so pitiful.

        • Aww, thanks Jasmin! Time machine hugs rock! Just be sure to go back to my tropical Oliver Twist era, rather than my ‘does that home perm harbor lice’ era.

          I was impressed by your high-schooler-looks-10-years-old photo. I can totally commiserate. I once got into the zoo for free on “12 and Under” day… as a senior in college.

  1. Wow, Jaam. Your random system pitted some mammoth entries against one another today. Those last two matchups are like a Duke-UNC first round game in the NCAA tourney.

  2. A before & after thing would’ve been really cool here– the evolution of awkwardness. It might have made some of us feel a lot better about posting our less-than-feminine, “do you like seafood?”, ankle-zipper jeans photos.

  3. I like that winning one of these matchups essentially means that you lost.

    Caitlin–I think in the semis I’ll do before and after photos if I get permission from everyone.

    Trev–I slightly agree, but I think the difference is that John is wearing a costume (at least, I think he is), while that was what Sarah looked like on any average day.

    • Oh, I didn’t just mean that contest. I actually think the Kelli-Caitlin contest is closer than it seems too. While Caitlin’s blatantly ridiculous picture is getting lots of press, the subtle awkwardness of Kelli’s Golden Girls meets Billy Ray Cyrus haircut, painting teddy bear sweatshirt over a turtleneck, and matching(?) heart-shaped yellow earrings are not to be overlooked.

        • It was that ridiculousness that made me that much more awkward. I didn’t just look the part; I was dorky through and through. Wish I could say that part has changed. *sigh*

    • My bad, Brad. Facebook kept telling me last night that it wasn’t going to post that status, so I kept clicking “Post” with varying degrees of aggressiveness until it worked.

  4. I was first upset that I missed the deadline. I’m still awkward, so my middle school years would have, I originally believed, been strong contenders. In 6th grade, for example, I still had late 80s/early 90s forehead-explosion bangs with a gelled perm, rainbow dangly earrings, a rainbow-colored sweater over an awesome turtleneck. I’m sure there were tapered-leg stonewashed jeans paired with this ensemble–wait, no, they were actually purple–but that’s just an added extra bit of knowlege for they can’t be seen in school pictures. However, when I saw the pictures that were submitted, I immediately knew I would never win. Not with the tie-bedecked science fair-at-home entry. Not with the photo-bombing cat and western wear. Not even with Jamey’s 90s jorts.

    And most definitely not with Sarah’s pure awkward awesomeness.

    I picture Sarah reading about this contest and immediately knowing exactly where this picture was located without hesitation, happy that this picture will finally get the credit it deserves.

    That picture made me laugh so incredibly violently that I literally have tears (plural) running down my cheeks and aching abs. That picture actually initiated the Silent Laugh, which is incredibly rare for me. It was at least a solid full minute of laughter before I made myself scroll down because it was starting to become painful. Every time I think of the button-anchored V-neck, I start laughing again.

    Sarah, this picture should be famous.

    • See, as much as I love Sarah’s photo and agree that it should be famous, what really got me was her description. I laugh out loud every time I read it.


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