“9th grade, 1999. I have no recollection of this school photo.”
“I was in an early 2000s transitional phase between awkward and total embarrassment.”
“In my defense, I was 16.”
Mom: “You’re going to regret this when you’re older.”
Me: “Hold my dagger.” Senior pictures, summer of ‘04
“My brother and I and our terrible haircuts and dye jobs, circa the early ’00s. Dyed-blonde bowl cut and bangs-only, respectively. We asked for these...”
“My mom dressed me like this so I was easy to spot when she picked me up...”
“My mother found this photo of my church friend (Ryan Gosling) and I. We had some awful ’90s haircuts.”
“You’ll regret this senior picture,” said my mom’s boyfriend. Turns out, he was wrong.
“I was a bit... extreme... And yes, I wore this daily, no matter what. I was 15.”
“I was a cute little girl, except for the fact that I’m a guy.”
“My mom said I wanted to keep my long hair, but I also wanted to use hair gel real bad. So, this was me in 1990.”
“Proof my parents hated me as a child”
“Mom got a new camera and I was her model.”
“Yes, that is me and my cat in a professional photo shoot. Thanks, mom!”
“The year was 2007. I watched America’s Next Top Model marathon and decided to do a high fashion photoshoot. Still waiting for a phone call from Tyra!”
“My lovely husband at 14. If only I had been so cool.”
“Me at 9, wearing all my favorite items of clothing at the same time”
“I knew I was cool and that is all that matters.”
“High school dance, eyebrows tweezed to non-existence, dreads created by glue...”
“Me, 12, thinking that Justin Bieber would fall in love with me if he saw me in the front row of one of his concerts.”
Bonus: Find the fake singer of the Backstreet Boys that looks like a young Steve Buscemi.
