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A Pollyanna is someone who is blindly optimistic about every situation, sometimes to the point of foolishness. The term is typically used in a negative way, to describe someone who cannot think about the more serious ramifications of various situations. Someone who behaves like a Pollyanna might be said to be Pollyannaish, which is why you might hear statements like “so-and-so can be so Pollyannaish about sales numbers.”
This term comes from a 1913 novel of the same name by Eleanor H. Porter. The heroine of the book, Pollyanna, is an orphan who is sent to live with her aunt in Vermont. In her childhood, Pollyanna plays a game with her father called “The Glad Game,” in which the two try to look on the bright side of every situation, and she takes the game with her when she goes to live with her aunt. Over the course of the book, she transforms the outlook of people living in her town, teaching them all to look on the bright side of life.
The book had a huge impact when it first came out, and it continues to be surprisingly popular; typically it never falls out of print, and a number of sequels have even been written to continue Pollyanna's story. The book is widely regarded by many people to be a classic of American children's literature, and it has certainly had a profound impact on American society. Some modern readers may find the book and its lead character a bit simplistic and childish, but something about it seems to resonate with people.
When the book came out, Pollyanna was undoubtedly designed to send a message to readers. Her unwavering optimism in the face of a variety of challenges was meant to remind readers that they could always find something good in a situation, even if the goodness wasn't always readily apparent. Even Pollyanna struggles with things sometimes, losing the use of her legs briefly after a devastating accident, but she ultimately decides to be grateful for once having the use of her legs in the first place.
There is certainly nothing wrong with a little optimism, but unrelenting optimism can sometimes be grinding for some people, especially in trying circumstances. Some people view constant optimism as evidence of childishness, though this is not necessarily always true. Generally someone who is accused of being a Pollyanna is also someone who refuses to see the truth in a situation, making it difficult to seriously discuss issues which must be dealt with.