Answer 1

Borrow money from a pessimist. They don't expect it back!

Answer 2

How many pessimists does it take to change a light bulb?
"Why does it matter? It's just going to burn out again!"

Answer 3

No sense being pessimistic. It wouldn't work anyway.

Answer 4

George: That man looked both ways before crossing the street. Now there's a true pessimist.
Hank: Why do you say that?
George: It's a one-way street.

Answer 5

A pessimist's blood type is always b-negative!

Answer 6

I held a festival of peace and meditation. My neighbors complained...

Answer 7

Yo mama so stupid if she got amnesia she'd get smarter.

Answer 8

"I joined Bachelors Anonymous. Whenever I feel like getting...

Answer 9

Answer 10