This guy is really angry at his girlfriend for making him wear this shirt. 

Whenever I'm sad, I like to draw men with long hair and who sing.

"It just goes to show, you can't base a society off a simile." Dr Doo Rag

This guy is expressing his disgust at yet another coffee shop opening on his block.

Lumbersexual Lovin'

Melancholy poncho girl

This girl's jersey is giving you flashbacks to a dog blanket you once saw at the SPCA 

but whatevs. 

Conversations with the boyfriend