So, just for full disclosure, I realized today that I made a mistake. I accidentally left out a contestant who submitted on time. Also, you all are having too much fun poking at each other, and I want to get in on it. Thus I’m entering my photo in the contest. If, by a long shot, I win the contest, I’ll give the whole prize pot to a charity of the runner-up’s choice.
These are the final three polls for round one. Voting will continue until Sunday at 1:00 pm CST. Good luck being super awkward!
Josh says: “In my defense, I’ve always heard that the camera adds ten pounds of head/glasses weight. You should have just called this the Tournament of Josh.”
Katie says:
My coworker, Cathy, is revolted by this photo from her younger years. I actually think she was kinda cute back in the day.
Speaking of cute…here I am, world. Your daily dose of handsome, coming at you from 1995 with slickly parted hair, a t-shirt that I’d never grow into, and a classic pair of jean shorts.
Jess says: “It was incredibly difficult to pick just one given my young tendency to dress in my parents’ castoffs and the absolutely terrible glasses that I wore. I’d estimate that I’m about 8 in this photo wearing an old nightgown of my mother’s under my dad’s overalls.”
Jess is the science experiment on the left. She says: “I am struck by the amount of self confidence I must possess to send this onto the internet with no “after” picture. But I have to respect that this poor little nerd had no idea that she would someday grow up to be nerd in better clothes.”
Katie (Josh’s sister–see first poll of today) says: “Josh asked Mom to send him any awkward pictures of himself that he could submit for the contest. In looking for his pictures she found pictures of me and suggested that I enter too because she thought I had him beat. I’m not sure if I should be flattered by her confidence in me or offended that she thinks I’m so much more awkward than him (because Josh had a few suuuper awkward years).”
That’s Trevor (T-Mac in the comment section) on the left and his sister on the right. I think she may beat the cat in John’s photo yesterday for Best Non-Contestant Creature in a Photo.














