sad guy in a beanie from EtsyThis has to be a common phenomenon, right? A free-spirited crochet queen forcing her boyfriend to model her handicrafts on Etsy? I found these twenty sad boyfriends pretty easily, so there are probably enough to at least launch a single-topic Tumblr blog.

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."
sad Etsy boyfriend

"Honey, I said smile."

"I AM SMILING."
sad Etsy boyfriend

He actually looks like he's been crying for a few hours.
sad Etsy boyfriend

This guy's thinking about Xbox.
sad Etsy boyfriend

Sadosaurus.
sad Etsy boyfriend

The faux wooden paneling is the saddest part of this photo.
sad Etsy boyfriend



The weight of the world is on this guy's hooded shoulders.
sad Etsy boyfriend

Grrrr.
sad Etsy boyfriend


I think this cheery guy is a designer at Tumblr.
sad Etsy boyfriend

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

The most unconvincing smile ever.
sad Etsy boyfriend

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

This is just getting ruhdiculous.
sad Etsy boyfriend

My personal favorite. Seething rage behind those eyes.
sad Etsy boyfriend

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

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

This guy thinks he's getting laid tonight.
sad Etsy boyfriend

He's sad because the beanie covers his bling.
sad Etsy boyfriend

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

Even this mannequin head is depressed.
sad Etsy boyfriend

After I wrote this, I noticed Regretsy found the saddest boyfriend of all.

... and if you liked this post, you should also check out Urlesque's 22 Examples of Etsy Child Abuse.