Content Warning: This section of the guide includes discussion of illness and sexual content.

Sydney Blake is one of the main characters and first-person narrators of the novel. The chapters titled with her first name are written from her first-person perspective and depict episodes from her storyline. In the narrative present, Sydney is pursuing her college degree in music. She’s wanted to “become a music teacher” for many years, but later in the novel considers “going into psychology” instead (311). She’s an intuitive, sensitive character who shows emotional depth both in her internal monologue and in scenes of dialogue. Her thoughtful character traits thus authenticate her interest in psychology.

When the novel opens, Sydney has just begun a relationship with Ridge Lawson. In the previous Maybe Someday novels, Sydney and Ridge had an emotional relationship. They didn’t act on their feelings—with the exception of their one kiss—because Ridge was in a relationship with Maggie Carson. Sydney is thrilled to be with Ridge in the present but has lingering guilt for kissing Ridge and betraying Maggie. Her remorse over this incident proves that she’s reflective and empathetic. She acknowledges that her behavior isn’t unlike her former best friend Tori’s behavior when she had an affair with her now ex-boyfriend Hunter.