The memories of Cynthia Rose that formed the lyric are from when she was 12 years old and in 6th grade - the last year Susannah Melvoin (and her sister Wendy, also a Prince associate) went to school with her. That's the year their teacher was Ms. Kathleen, who would greet the kids one by one as they entered the classroom.
According to Susannah, Cynthia was a very odd duck who lived in her own little world. She was weird, but of the 25 kids in the class, she was the only one who really stood out. In 2016, Susannah Melvoin launched a Starfish and Coffee website
, where she wrote: "Cynthia never had much interest outside of her own personal space, so watching her was an unedited version of what was going on her head."