Filed under: Humor, Fashion, Photos

Most of them are wearing beanies. Can a man be happy wearing a crocheted beanie? Anyway, hope you enjoy these pathetic sad sacks as much as I did.
"Smile sweetheart."

"Honey, I said smile."
"I AM SMILING."
He actually looks like he's been crying for a few hours.
This guy's thinking about Xbox.
Sadosaurus.
The faux wooden paneling is the saddest part of this photo.
The weight of the world is on this guy's hooded shoulders.

Grrrr.

I think this cheery guy is a designer at Tumblr.

I guess when your hair is that colorful, you need to tone it down with grays and a sad face.

The most unconvincing smile ever.

Did your girlfriend just get in a car wreck or are your earlobes just cold?

This is just getting ruhdiculous.

My personal favorite. Seething rage behind those eyes.

I want to stick little felt Bible characters on this guy's hat.

He's contemplating suicide by hanging himself on the chinstra---I dunno.

This guy thinks he's getting laid tonight.

He's sad because the beanie covers his bling.

The face of a man who suddenly feels like he doesn't even know her anymore.

Even this mannequin head is depressed.

After I wrote this, I noticed Regretsy found the saddest boyfriend of all.
- related:// The 24 Craziest Finger Puppets on Etsy
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