Jonathan, Phoebe’s best friend and roommate, is a dynamic and round character who serves as both Phoebe’s primary support system and a parallel figure in a journey toward self-acceptance. He decade-long friendship with Phoebe foregrounds Averick’s thematic exploration of The Value of Platonic Relationships. He acts as a constant source of stability and unconditional love for Phoebe, whether he’s reattaching her car mirror, comforting her during a panic attack, or picking her up when she’s stranded in Carl’s Jr. parking lot.

Jonathan’s outward confidence and ease with people in any situation represent an aspirational ideal for Phoebe, who frequently experiences anxiety and insecurity in public settings. Despite his outward confidence and kindness, Jonathan is deeply conflicted, secretly grappling with his own identity as a closeted gay man. This internal conflict makes him increasingly secretive about his personal life, creating a communication barrier with Phoebe that drives a rift between them for the first time. He resents Phoebe’s obsession with her romantic prospects because it forces him to confront the life he feels he cannot have. When Jonathan’s relationship with Finn is revealed, both Jonathan and Phoebe must face the things they’ve each been avoiding: Jonathan admits that he wants to live his life openly and authentically, and Phoebe recognizes she can no longer treat her friendship with him as a substitute for the romantic partnership she fears pursuing. Jonathan’s decision to come out to Phoebe reinforces the deep trust within their friendship.

Jonathan’s arc mirrors Phoebe’s in its exploration of societal pressure and hidden anxieties. Just as Phoebe feels trapped by the timeline for losing her virginity, Jonathan feels trapped by his conservative upbringing and his fear of his family’s rejection. He explains that he spent his twenties “pretending to be someone [he’s] not” (226) and worries it is “too late now, starting over at nearly thirty” (226). Phoebe draws on her own recent epiphany to reassure him that no timeline governs self-discovery. His arc concludes with him taking the first steps toward living authentically, demonstrating that platonic love can provide the courage needed to embrace one’s true self.

Matthew, Phoebe’s primary love interest, is a round and largely static character who represents the possibility of a genuine, patient, and accepting romantic connection in Phoebe’s life. In contrast to the manufactured meet-cutes on Phoebe’s list, her relationship with Matthew evolves slowly via their love of online word games—a shared activity that carries less physical pressure than the dates her list prescribes, allowing them to connect intellectually before the pressures of physical intimacy enter the relationship. Unlike Phoebe’s other romantic prospects, Matthew has known and admired her since high school, giving their relationship a foundation of pre-existing understanding and respect.

Matthew’s most defining trait is his patience. He is consistently understanding of Phoebe’s anxiety, even when she lies to him and cancels their dates. After she confesses everything to him, from her intimacy-induced panic attacks to her virginity, he does not judge her. Instead, he validates her feelings and offers to “take it slow” (237), giving her the control and security she needs. His own minor anxieties, such as his fear of eye drops, allow Phoebe to feel a sense of safety, trust, and companionship with him. Matthew’s steady presence gives Phoebe the space to experience intimacy at her own pace.

Nora, Meg, and Alex function as a collective support system for Phoebe, representing different facets of the contemporary dating landscape and serving as foils to her anxious perspective. As a group, they are fiercely loyal and loving, underscoring the value of platonic relationships by consistently supporting and encouraging Phoebe. Phoebe describes her friends as “My other greatest accomplishments: Jonathan, Meg, Alex, and Nora […] I think of them as my family. It’s not lost on me how rare it is to have friends like them as an adult” (13). However, Phoebe also consistently defines herself in opposition to them. She notes that “no matter how great they are, there’s a small part of me that feels disconnected from them. I can’t relate to their stories of sex and dating, and they can’t relate to my lack thereof” (13), highlighting the isolating experience of anxiety.

Across her arc, the varied experiences of Phoebe’s friends teach her there is no one “normal” way to experience love and romance. Nora is sexually liberated and confident, frequently pushing Phoebe to be more assertive and to “show off her assets” (35). However, her carefree approach to dating masks her own emotional exhaustion and desire for a meaningful connection. Meg remains empathetic and nurturing, even in the wake of her own painful breakup, leaning on romantic platitudes to stay positive rather than dwelling on the negative. Alex, who is romantic and sensitive, shares Phoebe’s tendency to fall hard and fast, but his own insecurities sometimes cause him to be more critical of himself and others. Together, their shared experiences provide a backdrop against which Phoebe’s learns to navigate her own.

Finn Evans is a flat character who plays a key role in Phoebe’s emotional growth and serves as a romantic red herring in the plot. As the handsome and kind new fourth-grade teacher, he becomes the primary target of Phoebe’s list-driven quest to lose her virginity. She views him as a “fresh start” (77) and projects her romantic ideals onto him, seeing their workplace interactions as signs of a budding romance. For Phoebe, he represents a straightforward path to achieving her goal, devoid of the emotional complications she feels with Matthew.

The reveal of Finn’s romantic relationship with Jonathan provides a moment of reckoning that pushes both Phoebe and Jonathan toward greater self-acceptance. For Jonathan, the exposure of his relationship with Finn pushes him to acknowledge his sexuality and his desire to begin living more openly as his authentic self. When Phoebe discovers that her perceived connection with Finn was a misunderstanding, it shatters her reliance on manufactured fantasies, pushing her toward genuine self-reflection. Phoebe recognizes that she’s used her preoccupation with Finn to avoid working through the anxiety she feels around her genuine connection to Matthew.

Sandy is Phoebe’s therapist and a mentor figure in the narrative. She provides the clinical framework for understanding Phoebe’s condition, labeling it as a phobia of intimacy and diagnosing her with panic disorder, OCD, and generalized anxiety disorder. Sandy consistently acts as a voice of reason, offering practical coping strategies to help Phoebe manage her symptoms. She challenges Phoebe’s self-deprecating mindset and the arbitrary timeline she has imposed on herself, encouraging her to focus on self-acceptance and let everything else happen in its own time. While Phoebe often resists her advice, Sandy’s guidance provides the underlying therapeutic principles that Phoebe eventually comes to understand on her own.