Skip to content

Behind The Awkwardness

Put On A Happy Face

“This is my older sister and I in 1985. I was only a year old and she was three. This picture represents how she pretty much manhandled me through most of our childhood. But I thought she was the greatest and eventually gave in and just did whatever she told me to do. Luckily, we had another sister with whom we teamed up and tortured together.”

(submitted by Stacey)

The Nosebleed

“This is a picture of my 6 year old daughter Isabella with a lovely tampon in her nose.  She remembers EVERYTHING and at some point in her life, I must’ve told her tampons were for nose bleeds.  She busted into my room one day with a bloody nose and remedy.”

(submitted by Toni)

Princess Complex

“Sadly, this is me. Hats off to my husband for marrying a girl with THESE issues.”

(submitted by Cheri)

Adventures In Babysitting

“This is a picture of my brother Jason. His babysitter’s son and him got in a fight.  Not wanting to cancel their professional portrait appointment, the babysitter thought this would be a good way to say sorry to our mom.”

(submitted by Lauren)

The Thing

“My mom, her sisters, and their parents on a vacation in 1972. We still have no idea who the specimen in the background is or what he is doing.”

(submitted by Ashlyn)

Boogie Nights

“My Uncle Scott…. ‘And here I was at a crossroads in my life. Should I continue to sell women’s shoes…. go off to college…. or leverage the mustache and pursue a career in porn?'”

(submitted by Emily)

‘Til Death

“Taken by our wedding photographer, and totally took me by surprise! I guess the stress was getting to my husband, or I had possibly been Bridezilla? Either way, this is still our favorite wedding photo–even after 20 years.”

(submitted by Janet)

The New Look

“This picture is of my grandfather meeting his first grandchild. Well, it was supposed to be. The picture is now actually of my grandfather being distracted by his 24 year old daughter, mortified by her piercings and crazy [awesome] hairdo. Clearly, a picture tells more than a thousand words here.”

(submitted by Lou)

Baby You’re A Firework

“This photo of me and my parents on the Fourth of July. Every year, our neighborhood has a parade and this year in particular my dad went all out making us wear these awful costumes. I was very upset because all of my friends got to ride their bikes in the parade and I had to wear the costume with my parents. My dad still considers these outfits a success because they got us a photo in the newspaper.”

(submitted by Jamie)

I Love You To Death

“The couple on the right are my great-great grandparents. I have no idea why they are pointing guns at each other.”

(submitted by Meagan)