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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 panglossian 

one who thinks that this is the best of all possible worlds, and screwed up as it may be, can't get any better.
She didn't bother to get out of bed anymore, her pessimistic panglossian perspective made life seem pointless.
pessimistic panglossian by sircasey February 15, 2009

Pessimistic Penelope 

A girl who always thinks things will turn out for the worse.
KPF: "My uniform got stained with gum but I think it will vanish overnight."
HBR: "No it won't."
KPF: "Well I think you're just being a Pessimistic Penelope."
Pessimistic Penelope by xenophyler December 14, 2010

Pessimistic Tourism

A type of tourism in which people will visit somewhere specifically because they believe that it is endangered in some way or another. For example, people visit Antarctica or rainforests and other untouched natural wildernesses as they believe that it will be destroyed due to climate change and direct human action in the near future and want to visit it whilst they still can. People might also do the same for man-made areas before they are supposedly torn down or otherwise closed or repurposed.
Those who visit Antarctica or glaciers solely because they know it is melting and will soon disappear are engaging in pessimistic tourism.

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.

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.