Delilah is the other dynamic, round protagonist of the novel and acts as a foil to Jackson. As a television weather reporter, her professional persona is one of relentless optimism and whimsy. This “sunshine girl” exterior, however, is a sophisticated coping mechanism developed in response to her own childhood abandonment. Raised by her grandfather after her mother, a violin prodigy, chose a career over motherhood, Delilah harbors a deep-seated fear of being “too much.” Her effervescent personality and tendency to find joy in chaos are her ways of ensuring that she’s always wanted and never a burden. This behavior, while authentic to her nature, is also a shield, preventing others from seeing the vulnerability and insecurity she hides. 

Delilah’s character arc is a journey to reclaim her professional and personal value without sacrificing her authentic self. The novel uses her career to explore The Struggle to Combat Workplace Sexism, as Keith consistently attempts to undermine her credibility by casting her in unserious roles, culminating in her demotion to a less visible features department. Her impulsive decision to quit live on air is the first time she publicly breaks her carefully constructed persona, choosing personal fulfillment over a prescribed sense of professionalism. Her relationship with Jackson catalyzes her character arc from a team player who never “want[s] to step on any toes [or] make a fuss” to a person who advocates for herself (248). Delilah pushes Jackson out of his comfort zone, while he provides the stability she needs to feel safe being messy and imperfect. He validates her professional competence, acknowledges her intelligence, and ultimately demands that she stop settling for less than she deserves.

Through her interactions, Delilah learns to set boundaries and act as her own champion. The Post-it note contract she signs with Jackson marks the beginning of this shift, as she establishes terms for their partnership. By the end of the novel, she’s brave enough to confront Ava Monroe, the president of the media company, with an impassioned defense of her value and her vision for community-focused journalism. She successfully gets her job back and ousts Keith by asserting that her joyful, empathetic approach is a strength rather than a weakness. Her journey is about integrating her inner vulnerability with her sunny exterior, realizing that she can be both a joyful optimist and a serious, respected professional.

Keith serves as the primary antagonist of the novel. He’s a static and flat character defined by professional jealousy and a misogynistic worldview. As Delilah’s boss at YBAL News, he epitomizes her struggle to combat workplace misogyny. As a man clinging to his past success as “the Face of Baltimore” (35), he resents Delilah’s natural popularity with viewers, which he perceives as a threat to his authority. Rather than valuing her connection with the audience, he actively sabotages her career by assigning her demeaning segments. As Delilah reflects, 

I don’t know when Keith started explicitly taking joy in watching me humiliate myself, but it’s been a slow slog through hell. I’m tired. I’m so tired of him scraping the bottom of the barrel and assigning me whatever he dregs up […] I’ve reported live from Fort McHenry while wearing a colonial dress two sizes too big. I’ve reported with an actual monkey on my head (15). 

Borison reveals that Keith’s animosity is rooted in envy and misogyny. Keith’s attempts to control the narrative—by canceling Delilah’s hotel room, removing her from the storm broadcast, and ultimately demoting her—are consistently thwarted by the solidarity of her colleagues, illustrating that his power is less absolute than he believes. His eventual forced retirement signifies a victory for a more modern, empathetic workplace and a rejection of his outdated, prejudicial leadership style.

Penelope and Adeline are Jackson’s 15-year-old twin sisters, for whom he’s the legal guardian. As round, dynamic characters, they function collectively as the heart of Jackson’s non-traditional family structure and the primary motivation for his personal growth. They’re keenly aware of Jackson’s rigid and serious nature, affectionately calling him predictable and encouraging him to embrace new experiences, like the television partnership with Delilah. 

The sisters serve as an important narrative device, offering an external perspective on Jackson’s transformation and acting as enthusiastic supporters of his budding romance. The twins also have their own significant subplot revolving around their estranged mother, Camille. Adeline, the “hopeful one,” wants to believe that their mother can change, while Penelope shares Jackson’s cynical caution. This conflict allows the novel to explore the complexities of biological versus non-traditional family bonds, culminating in Adeline’s realization that the consistent, loving presence that Jackson provides is more than enough.

Aiden, who’s also known by his on-air persona, “Aiden Valentine,” is the host of the radio show Heartstrings and Jackson’s best friend. He acts as a foil and mentor to Jackson, having recently undergone his own emotional journey from a surly and difficult loner to a man in a happy, committed relationship in First-Time Caller, the previous novel in Borison’s Heartstrings series. Because of his own experiences, Aiden is uniquely positioned to understand Jackson’s reluctance to embrace vulnerability. He consistently challenges Jackson’s self-imposed rigidity, pushing him to confront his feelings for Delilah and offering practical support, most notably by caring for Penelope and Adeline during the storm. Aiden’s character reinforces The Strength of Non-Traditional Family Bonds, representing a stable, reliable male figure in Jackson’s life who offers both emotional guidance and unwavering loyalty.

Maggie is the manager of the 101.6 LITE FM radio station and a mentor figure to both Jackson and Delilah. She’s a sharp, competent, and fiercely protective leader who orchestrates the central partnership, seeing the potential in bringing Jackson and Delilah together. Maggie’s confidence in Jackson’s abilities is unwavering, and she creates the opportunity for his promotion and professional growth. She also recognizes Delilah’s talent and worth, offering her a job at the radio station as an escape from Keith’s toxic management. Her subplot involving the attempted corporate takeover by Orion Communications and its vice president, Cooper West, highlights her dedication to preserving the local, community-focused nature of her station. It also lays the groundwork for the next book in the series, Longtime Listener, scheduled for publication in 2027, which is centered on Maggie and Cooper’s developing romance. Maggie represents an ideal form of leadership: one that is strategic and business minded yet deeply invested in the well-being and success of her employees.

Camille is Jackson’s estranged mother, a mostly off-page presence whose past neglect is the source of his control issues and fear of abandonment. Throughout the novel, Jackson struggles with how to handle his mother’s desire for a relationship with his sisters. He reflects, “Camille says she wants to be involved in the girls’ lives. Adeline and Penelope are old enough to make their own decisions, but I’m having a hard time putting them in a position where they could get hurt. Like I was. Over and over and over again” (268). Camille’s brief, unreliable reappearances create conflict for Jackson and his sisters, reinforcing the pain of inconsistent and unpredictable parental relationships.