Das's Law of Optimism/Pessimism 

The glass is twice as big as it needs to be. Get there.

Das's Law of Optimism/Pessimism is derived from something said by George Carlin. It explains that sometimes you expect too much of yourself and it gets you down in life.

Das's Law of Optimism/Pessimism by Mindbladeskillyaks June 16, 2010

Cautiously Pessimistic 

An increasingly relevant wordplay on the cliché "cautiously optimistic". As the world continues in free fall, its much more realistic to expect negative outcomes. Therefore, its much more pragmatic to maintain a cautiously pessimistic demeanor, rather than a cautiously optimistic one.

My cat is always cautiously pessimistic when inspecting anything new that I bring into the house.

Cautiously Pessimistic by ChimneySweepGreg August 10, 2012

pessimistic pete

Easily the most negative person in a group of people that are otherwise having a great time. But instead of keeping it to himself, it becomes his mission the fuck the fun up for anybody that looks too happy.

BRO 1: Hey I got these four girls to come back to chill with us at the house!

BRO 2: these girls don't like you bro, they're just gonna smoke your shit up, drink the liquor and leave. I bet at least two of them have the herp, either way this shit is weak don't bring them over I got shit to do at noon tomorrow.

BRO 1: never fails always such a fucking pessimistic pete..

pessimistic pete by Cpt.AMERICA August 27, 2010

pussimist 

someone who feels they are in a hopeless situation with a girl

John: I dunno man, I don't think she'll ever like me.
Richard: Stop being such a pussimist, bro. She'll come around.

pussimist by the capital T truth June 11, 2006

pessimist 

1.) A person who is known for their negative outlook upon life.

Related: cynic

Katie: You are such a pessimist!

Dante: You are going to die, too.

pessimist by Manawski February 23, 2003

pessimist 

Someone who is rarely disappointed, but sadly, very rarely pleasantly surprised.

A pessimist is a misunderstood realist, who would like to visit the planet optimists live on, but wouldn't like to live there.

pessimist by caster1 January 17, 2008

Pessimist 

What people now call a realist.

It's not pessimistic to acknowledge a cup half empty as long as you know its also half full.

Pessimist by Lucinda Belle 444 November 26, 2015