Hold Please - Mom

Hold Please

Please don’t text and deliver.

(submitted by Jen)

Squeezebox - Behind The Awkwardness


“This picture was taken in a photo booth that was quite small. We all tried our best to fit..well…this was the end result!! It has been one of our most treasured family portraits for years!!”

(submitted by Charlene)

The Arrival - Halloween

The Arrival

No amount of lamaze could have prepared her for this.

(submitted by Denise)

Backbreaker - Family Portrait


Picked the wrong day to wear ankle-highs.

(submitted by Shantal in Canada)


Mr. Ed - Pregnancy

Mr. Ed

Your caption here.

(submitted by Casey)

Horse Feed - Halloween

Horse Feed

Chew on that, Barbie.

(submitted by Jamie)

Sim-ifying the Awkwardness - Photos

Sim-ifying the Awkwardness

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.


To Each Their Own - Family Portrait

To Each Their Own

They agree to disagree.

(submitted by Christine)

awkward sweater, holiday pictures

Chastity Sweater

Two subjects you don’t often see in the same sentence.

(via © Gummbah+Chantal Rens at www.nobodyforever.com)