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Define Optimistic Pessimism Meaning

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 isn't bad.
By Liuka
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.
By Lilyan
Optimistic Pessimism
Saying something so blatantly obvious that's negative (a bad thing), but is covered up by making it sound "good"; encouraging words of apathy. It's like sarcasm, but not really.

An example of Optimistic Pessimism would be exclaiming, "Oh boy! I can't wait to fail the next test :D!"
Or maybe even, "Who wants to give up on life? I know I am!"
Anything that's negative can always be said in a positive way, and vice versa. Which is why sadists, jokesters, fixed-mindset people, etc., use this technique for their "humor" and "Socialish (Language)". But I digress.
By Sela