Bobby

Bobby is Bailey’s boyfriend and a senior at her school, presented as both a seemingly ordinary teenager and a source of unease within the Michaels household. His place in Bailey’s life brings her father’s protectiveness and Hannah’s uncertainty into the open, while his response to an insult about her father reveals a more protective side than those tensions alone suggest.

Identity and Introduction

Bobby is University of Chicago-bound and heads the student government. Hannah describes him as nerdy and, on the surface, a good guy; she also notes that he has no purple streaks in his hair, a detail that distinguishes his appearance from the image she associates with Bailey’s rebelliousness. The qualifications in Hannah’s assessment matter: Bobby seems harmless to her in some respects, but she does not know him well enough to feel certain of that judgment.

His introduction is linked to a joint Bailey offers Hannah. Bailey says that its use is legal in California, and Hannah suspects Bobby may have supplied it, though the source is not confirmed. The moment adds an uncertain edge to Bobby’s influence: Hannah is trying to understand what Bailey is doing and who may be shaping her choices, while Bailey gives little explanation.

Relationship with Bailey and the Michaels Household

Bobby is more or less Bailey’s boyfriend, and their relationship reaches beyond private time together. Hannah observes that after Bailey spends time with him, Bailey sometimes comes home and directs an insult at her. Hannah believes Bobby encourages Bailey’s disdain for her, though the text presents this as Hannah’s assessment rather than an independently confirmed intention on Bobby’s part.

Owen distrusts Bobby. Hannah initially tries to interpret that suspicion as overprotectiveness, but Owen has been less able than she is to brush aside the strain between Bobby and Bailey’s family. A few weeks before the scene Hannah recalls, Owen argued with Bailey because he thought she was seeing Bobby too often. During that argument Bailey gave Owen the dismissive glare she usually reserves for Hannah, making Bobby’s relationship with her a point of conflict between father and daughter as well as a source of friction for Hannah.

When Bobby comes to the house while Owen is away, Bailey makes clear that she wants him there. She says she will keep quiet about her father’s special delivery but insists on seeing Bobby; Hannah agrees on the condition that the two stay downstairs. It is the first time Bobby has visited when Owen is not home, and the first time Hannah must manage the situation on her own. From the living room, she sees Bailey snuggled against Bobby on the couch as they talk quietly. The scene looks harmless, but Hannah’s unease persists: she does not know what harmless looks like in this new responsibility. Bailey notices Hannah watching and shuts the glass living-room door with a deliberate thud, a symbolic barrier that does not actually prevent Hannah from seeing her.

Conflict and Protective Action

Bobby’s connection to Bailey is not defined only by her hostility toward Hannah or Owen’s distrust. Bailey later recounts that classmates whisper about her father and about her, as though she cannot hear them. One example is Brian Padura asking Bobby after chemistry whether Bailey’s father was a criminal. Bobby punched him in the mouth. The act is a sharp counterpoint to Hannah’s belief that Bobby feeds Bailey’s contempt for her: in this instance, he responds physically to an insult directed at Bailey’s family, and Bailey presents the incident as part of the school’s treatment of her.

The account does not settle Owen’s concerns or explain Bobby’s motives beyond this specific response. Instead, it leaves Bobby occupying an ambiguous position in Bailey’s life: a boyfriend whose presence intensifies family tension, yet also someone who acted against a classmate’s accusation about her father. That contrast makes him part of the novel’s depiction of Hannah’s uncertain stepmother role, where apparent danger, ordinary teenage intimacy, and acts of loyalty are not easily separated.