Chelsea Handler
"I know, I know. But my math teacher still wanted to penetrate me."
Brad Wollack
"I'm 15 here. At that time, President Clinton was hooking up with more young girls than I was."
Heather McDonald
"I'm wearing an off-the-shoulder black sequin mini dress that I wish I still had because it is totally in right now. The earrings and the hair, not so much. I remember my date's hands were all scratched up from rubbing up on me at the dance."
Chris Franjola
"Unlike the rest of my classmates, I got my picture taken at Now & Forever Wedding Photography. The popped collar was my idea…still like it."
Jen Kirkman
"I swear I'm not on drugs. I'm just trying to look tough."
Jeff Wild
"Little do I know, the day after taking this picture I will break out in terrible acne for the next 10 years of my life... LOL"
Sarah Colonna
"Hi, I'm Sarah. I already have curly hair, but still decided to get a perm. Call me."
Steve Marmalstein
"It's 1982, Chelsea can't hurt me yet."
Josh Wolf
"The worst thing about this picture is that I know it's the least embarrassing one of the night."
Fortune Feimster
"Future comedian, softball coach or UPS driver."
Roy Handler
"Marthas Vineyard, late '70s. The most incredible summers, as you can see by my form."
Chuy Bravo
"This is my nephew. Two days after this photo was taken he was as tall as me."