Sydney Shaw is the protagonist and one of the primary narrators of The Boyfriend. She appears only in the “Present Day” plotline, which Freida McFadden narrates from Sydney’s point of view. She is 34 years old but claims that “most people think [she’s] in [her] mid-twenties” (39). McFadden describes her as having brown hair with “natural blond steaks” and eyes that are “an intriguing gray color” (39). These relatively neutral descriptions offer a stark contrast to Daisy, Tom’s other romantic interest.

McFadden characterizes Sydney as a hopeless romantic who allows her desire to be in a romantic relationship to cloud her judgment. She begins her Cynch journey looking for “a decent man who doesn’t have a drinking or gambling problem, who is fun to talk to, who has a nice smile, and who likes [her] as much as [she] like[s] him” (39). Although she has a successful career, she admits that, “even in college, I was preparing for the eventuality of getting married and having children” (46). These passages reflect Sydney’s sincere desire to be married, and suggest that she centers her life around that goal. As a result, she’s willing to dismiss a number of red flags about Tom that push the plot’s mystery forward.