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Pessimistic Optimist 

It has many meanings such like :
- taking a precaution to prevent a near death experience
- level of optimism
- they see the cup as nor half full or half empty as to them it is constantly filling whilst constantly emptying
- for a good thing to happen a bad must follow and vice versa
our everyday lives are contributed to by pessimists, optimists and pessimistic optimists. An example of this is that : the optimists invent the aeroplane (great invention defies gravity and stuff), then the pessimists come along and think “no I don’t like that” so they come up with the parachute. Hey presto two great inventions one from a hopeful lunatic and one paranoid hopeful. You have the plane but how about the glider? Once again the optimists make them and such the pessimists the parachute. Now who tests it? The pessimist won’t yet as the optimist trusts his handiwork to much he want to go without any safety so the pessimist stops him. Now no one’s testing it. “I know” they think and they go fetch Dave from the local cafe. Everyone say hi Dave...Now Dave is s pessimistic optimist and he loves the idea of just gliding down to earth however he doesn’t want to die if it goes wrong so he takes the pessimist’s parachute. This is one definition of a pessimistic optimist: taking a precaution to prevent death or severe pain.
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Pessimistic Optimism 

When you thinking the worst will happen so when either it comes true or not, you either get the result you expected or you get delightfully surprised.
"How is Kyle so pessimistic and happy at the same time?"
"He is using Pessimistic Optimism"

Pessimistic Optimism

A mental state where a person hopes for a positive outcome while expecting or suspecting a negative one, holding both beliefs at the same time.
Her whole plan felt like pessimistic optimism—she wanted it to work, but you could tell she didn’t fully believe it would.

Optimistic Pessimism

Hope for the best; prepare for the worst.
Optimistic pessimism is a great way to live your life, because you can't lose.

People who argue that optimistic pessimism - or any kind of pessimism for that matter - is a self fulfilling argument are just naive irrational pseudo-philosophical hippies.

optimistic pessimism

telling yourself that the outcome of a situation will undoubtedly be pleasant; when knowing that the truth is that it will not, so that your artificial smile and laughter will not and cannot be undistinguished between true and false. ultimately living a "happy" and "carefree" lifestyle that many people envy, not knowing that you are as miserable as they are. you just dont show it in public as they do. your glass has water in it. whether it is half full or half empty doesnt matter, but there's water in it and it's constantly getting filled and consumed
optimistic pessimism by Jeremy Beck February 12, 2008

pessimistoptimist 

to be in a state of mind that fluctuates with the one(s) you enjoy being around

always have somthing to say that is taken good or bad at the same time
saying to your friends "you all such mucho balls" because they pulled a prank on you but directly after laughing about it
pessimistoptimist

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.