Cecily Gregory is a friend of Sophia Edwardson's from preschool who like Sophia loves to hang out with their best friend from kindergarten, Darienee Richardson. Besides that, Cecily is a major bookworm, even in kindergarten and first grade. After kindergarten, she studies the subjects talked about in school from first grade forward every day in the school year and even reads for recreation every summer break. In her personal life however, Cecily develops a small crush on Louis Benson which he readily returns the feelings for him about. Eventually in eighth grade, they become boyfriend/girlfriend and fall in love towards the end of high school.