Behind The Awkwardness

Father Knows Best

“This is a picture my mother-in-law sent me while I was at work of my husband and son. Husband is playing my son’s leap frog game while my son is in the background… under a plastic tote. Men.”

(submitted by Monai)

Wunderbras

“When I was a kid, my mom, who is a seamstress, would make funky gifts every year for Christmas. Some time in the late 80s, she got her hands on some giant men’s underwear and made sports bra’s out of them. Hence, my two aunts and grandma modeling them on Christmas Eve. This is just one of many awkward Christmas eve photos.”

(submitted by Tara)

The Last Samurai

“Our family trip to Japan ended in a professional photo shoot to commemorate the trip. This was the result.”

(submitted by Serena)

Intimidation Factor

“This cringeworthy shot was taken at my Uncle’s wedding. I’m on the far right, then my dad, grandfather, and uncle and for some reason, the photographer had us try to look intimidating. Well, I’m a photographer now and do a much better job preparing my subjects for a wedding photo.”

(submitted by Scott)

The Towel

“This is a recent photo of a family friend in the midst of her pregnancy. Nothing says tender loving mom-to-be more than a pin up bathing suit and sexy heels. The white towel is there just in case her water breaks.”

(submitted by Marie)

Insane Clown Posse

“This is my husband and his younger brother dressed as clowns.  Their Mother (my Mother-in-law) decided that for Mother’s Day one year that she would dress her 2 sons as clowns and have their portraits taken.  So, she proceeded to dress them up in homemade outfits and her own makeup.  On the way to Sears, the younger brother was crying hysterically and that is why he is not a “happy clown,” and his face is smeared.  I have this picture hanging in our hallway of our home just to remind myself that I am now a part of a dysfunctional but awesome family! Now we have two sons together ages 3 and 4… question is, should I carry on the tradition?”

(submitted by Whitney)

The Seduction

“This is a photo of my Ma and Pop out on a date in the ’80s. My mom must have followed the instructions on my father’s shirt, because 9 months later I was born!”

(submitted by Cleitus)

Jungle John

“Back in 95, a traveling zookeeper (Jungle John) came to my cousin’s birthday party and all the kids took pictures with him and his snake. Needless to say, I wasn’t into it. And I’m afraid of snakes and men in safari hats to this day.”

(submitted by Samm)