November 6th, 2014

Sweaterrific - Behind The Awkwardness

“I was going through old photo albums at my future father in-law’s house to scan childhood images of my fiance for our wedding slideshow. Both my fiance and his father are pretty masculine…played football, served in the military and in law enforcement…but somewhere along the way, my fiance’s former stepmother managed to dress the guys in these terrible outfits and drag them to an Olan Mills for what I can only imagine was one of the worst afternoons of their lives.”

(submitted by Kimberly)


November 6th, 2014

Solidarity - Behind The Awkwardness

“Barcley has this sore on his face that he won’t stop scratching. I avoided the cone for as long as I could but today was the final straw. He seemed so miserable I wanted to show my support.”

(submitted by Lane)

• In Behind The Awkwardness6 Comments »

Awkward Tees Have Arrived!

November 5th, 2014

Awkward Tees Have Arrived! - Photos

Get in touch with your inner awkward at awkwardandsons.com!


November 5th, 2014

Misery - Photos

Loves company.

(submitted by Coral)

• In Photos2 Comments »


November 4th, 2014

Roped - Engagement

Perhaps this one needed a second opinion.

(submitted by Britney)

Kicking And Screaming

November 4th, 2014

Kicking And Screaming - Christmas

Fortunately, this Santa works as a bouncer in the off-season.

(via LisaMariePhotography)

• In Christmas1 Comment »

Sim-ifying the Awkwardness

November 3rd, 2014

Sim-ifying the Awkwardness - Photos

In honor of the release of The Sims 4, we are proud to unveil the Sim-ifying the Awkwardness Gallery where the wonderfully weird inhabitants of our favorite video game recreate some of our classic awkward family photos.


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