Caravan
“Me and my brother. Dad brought car from the dump in the back of his van.”
(submitted by Noah)
Even More Behind The Awkwardness
Christmas Jazz Hand
“The infamous Christmas photo shoot of 1984. Dad’s short-shorts and high...
Slippery Slope
“Here I am 3 years old. My parents thought it would be cute to take my...
Run To The Hills
“This picture was taken circa 1985. I grew up the only Chinese kid in a very small...
Friendly Conversation
Even More Behind The Awkwardness
Eyes Wide Shut
“This is one of the many awkward engagement photos my fiance and i took. The...
That Guy
“During the summer of 1989, my BFF and I were staying on the beach with her...
This Magic Moment
“So I was going through some old photos and I found this. My Dad holding Magic...
Baby Powder
“This is a favorite early photo of my daughters after a strange incident involving...
Latest Awkward
Passion Rekindled
“It was supposed to be a nice family photo but instead it looks like a commercial...
Bill The Babysitter
“Bill Murray used to babysit my brother and me. Here’s a photo of us in the...
Imagine Dragons
“My sister asked me to draw a scary picture on her Barbie magna-doodle.”
The Concert Doppelganger
“I found my sister’s twin at the Coldplay concert in Gothenburg.”
Zoom Lenses
“This kid’s childhood was not always easy. Actually, it’s me 22 years...
The Fountain
“Perhaps I should have thought twice about leg placement when sitting on the...
Zardoz
Sir Sean Connery’s first post-James Bond role in 1974.”
Different Sides Of A Big Day
“Just got married. If there were ever a picture that summed up the different...
I’m With The Band
“My dad just handed me this and said, ‘This is my picture of R.E.M....
City Slicker
“My uncle had Billy Crystal as a camp counselor in 1967.”
Not Quite Paris
“So my friend proposed to his girlfriend like this.”
Shoulda Gone With “Pixie”
“So this came with my daughter’s craft set.”
Couple Wore Matching Outfits For 37 Years
Don and Nancy wore matching outfits for 37 years. Each outfit has been hand tailored by...
The Book Of Prom
“I’m over ‘promposals’ but my little brother’s actually...
Flower Man
“I was recently the flower MAN in a wedding. And it was awesome.”
Clown Recreation
“I recreated this awkward photo last year. The original is from about 1988. I must...
