Awkward Family Photos, the website that allows readers to share embarrassing family images, became an overnight success when it launched earlier this year. The creators of the site have now signed a ...

Yes, Ashton Kutcher knows he went viral last week because of those awkward pictures with co-star, Reese Witherspoon. The internet had a field day over how they stood next to each other at the premiere ...

Ah yes, the Blunder Years. That beautiful stretch of time when we all thought frosted tips were edgy, eyeliner was a personality, and posing with your arms crossed made you look mysterious instead of ...

On Jan. 21, Republican presidential candidate and Most Awkward Man Alive™, Ron DeSantis, suspended his campaign and officially endorsed Donald Trump for president in 2024. DeSantis ran as a far-right ...

Share your cringey prom photos with us for a chance to be featured in an upcoming gallery.

Life was much different before the digital age. We didn’t have instant access to information or the mundanity in the lives of our families, friends, and acquaintances. Photos were primarily private ...

See the funny photos Jasmine took with her husband, Brett Roth.

The Christmas season has generated some of the most awkward holiday photos we've ever seen. Whenever the entire family gets together, rest assured, there's going to be someone around snapping pictures ...