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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. She relates to Mary Anne. Dawn once saw her getting in to a van of high school guys while an ambulance was picking up her mom. She thinks about her mom every single minute and loves her more than anything. She gave her her favorite plant as a hospital gift. She once ran away to be with her crush, Carson, but had Ducky pick her up. After that, her parents said they would listen more. She got drunk at a concert and a party. In SS13, Dawn mentions her mother was doing well. She did not like her mothers support group. She hates hoping about her mom because the higher she hoped, the more dissapointed she was. She has her navel pierced and wore black makeup. Ducky McCrae sat next to her at her moms funeral. She and her aunt sat next to her mom until she stopped breathing. Her mothers last words were about her. Her father became a workaholic and always yelled at her. She had a kinship with Carol, and she was like a mother to her. She saved her when something was happening, but later she burned something because She was seeing her crush, beau. She started having a crush on Ducky. When she visited Stoneybrook, she snuck out to NEW YORk city. She is trying to get her life back together.

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