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Sunshine Daydream "Sunny" Winslow is Dawn's best friend in Palo City, California. Sunny's parents were hippies, which accounts for her unusual name. Her father runs a bookstore.

Sunny and Dawn grew up down the street from each other. They are alike in many ways. For instance, they both have long blonde hair, although Sunny's is more of a strawberry blonde. They both love healthy whole foods and neither of them will eat red meat. (One of Sunny's favorite foods is Mrs. Bruen's three cheese macaroni.) Both girls love surfing and ghost stories.

Sunny founded the California version of the Baby-sitters Club, the We ♥ Kids Club, with Maggie Blume and Jill Henderson (Dawn on the Coast).

Sunny went through a dark period after her mother was diagnosed with terminal cancer. She began skipping school and dating older guys (see California Diaries). Although the Winslow and Schafer families were still close, Sunny began to see Dawn as a goody-two-shoes. Her best friend during this time was probably Ducky McCrae. In another series (about Dawn and the We <3 kids club) it says Sunny's mom died.

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