Prior to the start of the novel, Averick’s Author’s Note directly frames Phoebe’s experience as a corrective to the “sexually empowered female leads” (vii) common in romance fiction. This context positions Phoebe’s anxiety as a deeply ingrained psychological condition that shapes the narrative’s core conflict rather than a temporary obstacle to be overcome. The prologue establishes the origins of Phoebe’s anxiety through a single formative scene. At a school assembly, her first near-kiss with Lucas Johnson ends with a panic attack that leaves her feeling humiliated and convinced that “There’s something really wrong with [her]” (4), beginning a pattern of self-blame that governs her life for the next 17 years. Averick juxtaposes Phoebe’s novel-inspired fantasies of a first kiss—”Would he tuck a strand of my hair behind my ear before he leaned in?” (2)—with the visceral, clinical description of her panic attack—“My throat is closing up” (4)—illustrating a fundamental schism between her internal desires and her body’s involuntary response. This contrast establishes the ways her deep longing for connection is continually thwarted by a physiological terror she cannot control, highlighting The Isolating Experience of Anxiety.

The letter from Phoebe’s 18-year-old self, which arrives a month before her 30th birthday introduces The Arbitrary Nature of Timelines for Social Milestones. The letter’s two-sentence directive, “Lose your virginity. That’s all I ask” (8), functions as self-judgment from Phoebe’s own past. Phoebe internalizes this message as proof of 17 years of failure, measured against a self-imposed deadline that has no inherent meaning outside of cultural pressure. Her sense of shame prevents her from seeing value in any other part of her life, leading her to dismiss her therapist’s suggestion to list her adult accomplishments as an “insult to the art of list making” (30). This shame prompts the creation of her checklist in Chapter 3, a central symbol in the novel. The list represents Phoebe’s attempt to meet the arbitrary timeline her younger self set. By having the pressure originate from Phoebe herself, the narrative demonstrates how thoroughly she has internalized external expectations about romantic and sexual norms.

In response to this self-inflicted pressure, the checklist Phoebe creates with her friends symbolizes her attempt to regain a sense of control over the chaotic and terrifying prospect of intimacy. After Nora jokingly pitches a movie title, “How to Lose Your Virginity in Thirty Days” (30), Phoebe seizes upon the idea and transforms it into the tangible, systematic effort to deconstruct romance into a series of manageable, predictable tasks. The items range from classic romance-novel meet-cutes—in which the romantic leads first encounter each other in an unexpected or humorous way—to modern dating realities (“Redownload Hinge”), reflecting an attempt to engineer the spontaneity she’s read about in her romance novels. Walking home from the bar with her list in hand, Phoebe reflects, “For the first time in a long time, thanks to my new list, I feel like I might actually be getting somewhere, like I might actually have some control (38). The checklist gives Phoebe a way to calculate quantifiable progress but fails to address the internal work of learning to effectively manage her anxiety.

Throughout the novel, Phoebe’s friends provide a constant source of stability, introducing the novel’s thematic emphasis on The Value of Platonic Relationships. Averick uses the device of the friends’ group text transcript to underscore the daily ways they engage with each other’s lives, look out for each other, and provide moral support. After a night out, Phoebe texts the group chat: “pulse check on Meg?” and Alex responds, “Sound asleep on my bathroom floor” (56). The easy closeness she feels with her best friend, Jonathan, also inspires fantasy scenarios rooted in romantic ideals rather than their reality, positioning Jonathan as a romantic red herring. Phoebe imagines the fanciful narrative of a romance with Jonathan but can’t reconcile it with their actual dynamic: “the friends-to-lovers trope has always been one of my favorites. So the idea of Jonathan and me being endgame is something that I can’t help but wonder about […] Would I want that? It feels wrong to think about Jonathan sexually, and even romantically” (21). The hints that Phoebe interprets as signs of a potential romance with Jonathan in these early chapters are all filtered through a fanciful lens—a misdirection from Jonathan’s true internal conflict over his sexuality.

Averick suggests that Phoebe’s tendency to construct these romantic narratives is rooted in her inability to see herself or Jonathan clearly. Her self-deprecating belief that he is out of her league neutralizes any romantic pressure and prevents her panic responses. Phoebe reflects, “Jonathan’s looks quickly became one of the reasons I’ve always been so comfortable around him. I’ve never had to worry about something sexual or romantic happening between us because there’s no way someone who looks like that could be attracted to someone who looks like me” (18). Across her arc, Phoebe learns to see both Jonathan and herself as they truly are. When the reality of a date with Matthew triggers Phoebe’s anxiety, it is Jonathan who provides the stability and reassurance necessary for her to take a small risk, helping her craft a non-committal response. He acts as an external regulator for her anxiety, offering a form of unconditional acceptance that allows her to confront her fears without judgment.

Averick contrasts Phoebe’s attraction to Finn and Matthew to bring Phoebe’s pattern of avoidance into sharp focus. The moment she receives an enthusiastic, text from Matthew—a man she already likes and whose interest is real—confirming their date, Phoebe immediately retreats into the safer, more distant fantasy of her crush on Finn. She tells Jonathan, “I definitely can’t go on a date with [Matthew] when I’ve spent a year thinking about him while I fall asleep. The stakes are too high. Finn is a fresh start. I think that’s what I need” (77). When Finn offers Phoebe a low-stakes infatuation, while Matthew represents an imminent, high-stakes reality that threatens to trigger her panic. Averick frames her pivot toward Finn as a form of self-sabotage, demonstrating how her anxiety moves her away from her own stated desire for growth.