23 Awkwardly Funny Family Photos

Cherished Memories:

Funny Family Photos Too Weird for Words

1980s High School piyearbok picture: Dude with big hair, mullet in Batman shirt


In Whitney’s defense, she thought it would help the herd produce more milk. Unfortunately, no one bothered to tell her they were beef cattle.

funny awkward family photos: girl flashing her boobs at cows


Teddy “The Turtle” Thompson. A spray tan so bright, ya gotta wear shades.

funny awkward family photos: bad spray tan photoshopped nose realtor


“Hi, Teddy.”

funny awkward family photos: 1980s family portrait sunglasses polka dots


Phyllis Jean, not believing one iota of the cockamamy bull dookie her sister Evelyn is bantering about.

funny awkward family photos: old woman drinking and smoking in backyard


Little Henry Lee, the first person on public record known to proclaim, “WTF!”

Vintage family portrait, creepy family, creepy baby


Wash the gator night at Great Uncle Cy’s.

vintage snap, man washing alligator in living room next to wood stove


Here comes Peter Cottontail, literally.

funny awkward family photos: crossdressing man easter bunny easter S & M


“Having fun, dad?” asked Colin. “Shoot me now.” dad replied.

funny awkward family photos: dad and son on amusement park ride


To the dismay of his parents, little Tommy X would grow to have a fondness for Celine Dion.

funny awkward family photos: 1980s family portrait, punks and baby, plan mills


Suddenly, Robert was crushed by a lonely, cold, harsh wave of inferiority.

funny awkward family photos: man looking sadly at giant carrot, feeling inferior


Francine vowed never to be late for Bingo ever again.

funny awkward family photos: grandma on motorcycle side car


Ahhh, springtime in Kentucky.

redneck vehicles; Convertible pickup truck on highway


Traynesha in her 4-leafed clover dress. Feeling lucky anyone?

Funny wardrobe fashion fails : woman with slits in dress 4 leafed clover look


Todd’s 11th birthday party just hit warp speed.

Funny awkward family photos: kids jacked up on energy drinks


Before Tiffany downed that last shot of Jägermeister, she raised a toast to her goal for the evening “to get a pole in my panties.” …Mission unaccomplished.

funny pics, drunk girl passed out and her clothes stuck on over street post


Ohhhhh… that’s why Costco was out of Ramen Noodles.

funny awkward family photos: man with huge white hair, brillo, ramen noodle head


After their numerous suggestion box requests to remove strained peas from the Shady Acres weekly dinner menu were denied, Frank and Leona decided to take matters into their own hands.

Funny awkward family photos: Grandma & Grandpa with guns


“Move aside, ladies. I’ve spied a hard target waiting in the wading pool.”

Funny awkward family photos. 2 woman posing for camera, little boy with hand down his pants


Another Tuesday night full of “come hither” looks from Aunt Donna.
Vintage snap: woman with big hair drinking & smoking, "I'm drunk what's your excuse" shirt


After years of searching, Ted finally found the Happiest Place on Earth.

Mardis Gras, women with Minnie Mouse faces on their boobs. Awkward funny fix


Happy Easter from creepy Uncle Buddy.
funny awkward family photos: creepy naked bunny man

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