Pessioptimist 

A person who is both an optimist and a pessimist.

Pessimism for the win!

(This is funny because a pessimist wouldn't ever say for the win, but a pessioptimist would.)

Pessioptimist by EchoSoul October 11, 2016

pessoptimism 

A philosophy that encourages forward-thinking optimism with an educated acceptance of a basic level of pessimism. Optimism's fault is it's naivete, pessimism's it's blind jadedness. We live on Earth and are human. There is, was and will be good and bad. Shit happens, dreams come true.

Hey kiddo, have a little pessoptimism. Keep your eye on the mountain, pretend the obstacles aren't there, but don't get too bent out of shape when there's a thousand miles, an abyss, a cougar and crossfire before you get there. And that's alright. The goal isn't really worthy without that stuff in the way.

pessoptimism by Jeffrey John September 19, 2007

pessoptimist

A pessimist and an optimist. An individual who combines pessimism and optimism into a cohesive worldview that is neither purely negative nor wholly positive. They are distinct from a realist as they do not engage in a pragmatic approach to life. Rather, they are the quintessential happy-sad person.

A pessoptimist is someone who sees the the glass as both half empty and half full, enjoying the fullness as much as despising the emptiness.

pessoptimist by Zek J. Evets December 30, 2016

pesoptimist 

Someone who wishes to cleanse the world...and be cheerful about it.

"The Pope says that we should create a disease to make 99.9% of the population die while laughing. She's a Pesoptimist."

pesoptimist by Lexi77 August 30, 2007