Toby Shaw

Toby Shaw is Bailey Walker’s boyfriend of two years and, after her death, one of the people most closely bound to Lennie Walker’s grief. First viewed by Lennie as an irritating outsider to her sister’s world, he becomes a companion in mourning: his memories of Bailey bring their happiness vividly into view, even as their grief draws them into an intimacy Lennie believes she should refuse.

Identity and Introduction

Lennie first encounters Toby in Bailey’s garden, where he is lying among two neighbor dogs, Lucy and Ethel, apparently taking a break from weeding for Gram. The setting is characteristically unceremonious: the garden’s blooming angel’s trumpets and lilacs make it easy to lie back and lose track of the day. Toby is embarrassed to be caught in that position, while Lennie arrives carrying a long-standing suspicion of him.

Lennie describes Toby as part cowboy and part skate rat. His mix of identities reflects the way Bailey first noticed him: she was waiting near a trailhead, imagining a romantic hero on horseback, when Toby appeared on a skateboard. He had ridden in from Clover High, where his ranch-kid and skater circles had previously kept him apart from Bailey’s drama-oriented world. For Lennie, that chance sighting marked the start of Bailey’s infatuation and her transformation into what Lennie regarded as a love-struck version of herself.

Relationship with Bailey Walker

Lennie resents Toby for seeming to absorb Bailey’s attention and for treating Lennie as unremarkable. His skateboarding skill does not soften her view; she thinks neither his cowboy persona nor his ability to perform difficult skateboard tricks makes up for the way Bailey’s romance has eclipsed their sisterly closeness. Her irritation is therefore less a neutral assessment of Toby than a measure of how much she misses Bailey’s attention.

Despite Lennie’s judgment, Toby and Bailey’s relationship is serious and enduring. When he tells Lennie that he has asked Bailey to marry him, he does so quickly, watching for her reaction. Lennie is stunned: both are nineteen, and she has thought of Bailey as wary of marriage. Later, Toby recalls Bailey’s wish to hold the wedding ceremony at Flying Man’s, where they could jump into the pool after exchanging vows. His account gives Lennie a concrete image of a future Bailey had imagined—an orange wedding dress, laughter, and a party making its way back toward the house—and makes the loss feel newly immediate.

Grief and Lennie Walker

After Bailey’s death, Toby’s grief becomes entangled with Lennie’s. Lennie’s account of their closeness includes an earlier night when they make out, an act she sees as a betrayal of her sister and of her own promise not to kiss him again. She is startled by the force of her desire, especially because her earlier experiences of physical intimacy had left her feeling detached rather than moved. In grief, Toby becomes the person she imagines when she kisses the air, and the attraction is inseparable from her fear and confusion.

At Flying Man’s, Toby and Lennie lie beside one another under the stars, close but not initially touching. He tells her how Bailey wanted the wedding to take place there. The imagined ceremony briefly restores Bailey’s joy in vivid detail; then Lennie begins to cry, Toby cries too, and they kiss. The scene makes their intimacy less a simple romance than a response to a shared absence: they are drawn together by the happiness they remember and the future that has disappeared. Lennie understands that being with Toby can make her feel less afraid, but the closeness also sharpens her sense that he was Bailey’s boyfriend and remains bound to her sister.

Narrative Role and Significance

Toby is presented chiefly through Lennie’s changing perspective. At first, she reduces him to the rival who has taken Bailey’s attention and sees him as indifferent to her. After Bailey’s death, the same relationship that once provoked Lennie’s resentment becomes a source of shared memory and comfort, while also placing Lennie in conflict with her loyalty to Bailey. Toby’s account of the wedding that never happens gives grief a specific, imaginable shape; the kiss that follows shows how mourning can create closeness without resolving the moral and emotional difficulty of that closeness.

Lennie later reflects that Bailey’s death has left her less sheltered from the world, and connects that changed intensity to her renewed desire to make music and to the possibility that Joe Fontaine noticed her because she was no longer holding herself inside a shell. Toby belongs to the painful earlier part of this awakening: their connection reveals how loneliness and grief can draw Lennie toward someone who shares her loss, even as she struggles to distinguish solace from a betrayal of her sister. The contrast between their imagined wedding and their grief-stricken kiss keeps Bailey present in their relationship, not as a rival to be displaced but as the person whose love and absence shape what passes between them.