Episode list

Back in 1990, five-year-old Arielle Vandenberg was invited to her single Mother's dinner date at home with her then boyfriend, Michael. Unfortunately, little Arielle's attempt to make everything perfect for her Mom went perfectly wrong.

Back in 2005, high school freshman Tessa Netting was suddenly doing the Suessical musical with all of the upperclassmen actors she idolized as a middle school! But, in the midst of having trouble fitting in, she had A LOT of trouble with some green foam ham props at rehearsal!

Back in 2010, 17-year-old Christopher James was hired to do magic at a bachelorette party. Problem is... did the bridesmaid's realize he's a magician?

Back in 2012, 18-year-old Meghan Rienks was a college freshman all set to go on an amazing date with a hunky senior film student. They went to a play, then to a college party, and it turned out amazing alright... amazingly awkward.

Back in 2013, Jonah Green attended a college party as a freshman that was absolutely perfect. Cool people, great music, and Jonah was the life of the party. Yep, he was total social butterfly. That is, until he did something so totally humiliating at the party he wished he could fly away forever!

Back in 1999, all 15-year-old Lana McKissack wanted to do was make a fabulous flan for her high school Spanish class, and update her 'do with some rad new bangs. Unfortunately, after numerous flubs, all Lana would be flaunting by the end of the day were her tears!

Back in 2012, Rickey Thompson was with his Mom for their weekly shopping outing. But when Mom decides to go inside a bra store, Rickey decides he'd rather go get a pedicure next door. That decision led to the most awkward moment of his life!

Back in 1999, 14-year-old Matt Cutshall found himself hanging out with the cool kids again. He was always shocked they wanted to hang out with him, but they'd ride bikes, play video games, or go swimming quite often. But, for some reason on this day, they wanted to do something called 'birding' by the pool. This led to a moment so humiliating for Matt, he had trouble talking to his older sister for days!