Bailey and Toby’s relationship

Bailey and Toby’s relationship moves from a vivid first encounter to a two-year romance and an accepted marriage proposal, only to be cut short by Bailey’s death. The engagement and the wedding they imagined make their loss more than the absence of a person: they leave behind a shared future that Bailey had chosen, Toby still hoped for, and neither could complete.

First encounter and courtship

Bailey first notices Toby when he passes her on horseback. She is absorbed in a novel and imagines him as the handsome Revolutionary from its romantic plot, a figure who rides up and sweeps a woman away. She is so captivated by the sight that she waits for him near the trailhead for hours, pretending to read. When Toby eventually comes back from the other direction, he is riding a skateboard rather than a horse. He is not a character from Bailey’s book but a student from Clover High who moves among ranch kids and skaters, while Bailey’s own social world centers on drama. The contrast between those circles had kept their paths from crossing before that day; afterward, Bailey’s first impression matters more than where he came from or what he rode.

The relationship lasts two years. By the time Lennie encounters Toby in Bailey’s garden after Bailey’s death, he is identified as her boyfriend of that duration. His presence also marks how sharply the family has been separated from him in the immediate aftermath: Gram has repeatedly urged the family to reach out, while Toby has been missing lately. When he finally appears, he is lying among two sleeping dogs, Lucy and Ethel, in the garden’s springtime quiet. He says he has been weeding for Gram, embarrassed by the ease with which Lennie finds him resting. The scene places him back in Bailey’s home and family orbit, but not yet at ease within it.

The proposal and Bailey’s answer

Toby later tells Lennie that he asked Bailey to marry him. He delivers the news quickly, watching her to gauge her response. Both were nineteen, and Lennie understands Bailey as someone strongly averse to marriage; the proposal therefore surprises her as much as the fact that Bailey accepted. Toby’s answer is yes. His hope remains audible even as he speaks to Lennie, while Lennie is stunned that Bailey wanted marriage and hurt that she had not told her sister.

The disclosure exposes a change in the sisters’ closeness as well as a commitment between Bailey and Toby. Lennie had understood Bailey and herself as the pair who told each other everything, so learning about the proposal only after Bailey’s death makes the secret feel like exclusion from a future that can no longer happen. Toby explains that they intended to tell the family the following week, after he had just asked. His use of we brings the planned announcement into focus as something Bailey and Toby meant to share together, not a decision Lennie could still discuss with her sister.

A future planned at Flying Man’s

Toby’s account of Bailey’s wedding plan gives their engagement a particular setting and an exuberant shape. He tells Lennie that Bailey wanted the ceremony at Flying Man’s, followed by a jump into the pool after the vows. As he speaks, Lennie imagines Bailey in a bright orange wedding dress, soaked and laughing as she leads the party back toward the house. The image is not a wedding that takes place; it is the future made vivid by Toby’s memory and Lennie’s imagining. Its happiness intensifies their awareness that Bailey is gone and that the celebration she wanted cannot be held with her in it.

The proposal, intended family announcement, and wedding plan together show that Bailey’s acceptance was not merely an abstract answer to Toby. They had begun to imagine how to make the commitment public and how to celebrate it with people close to them. But the account reaches Lennie only after Bailey has died, when even the couple’s plans arrive as information that cannot be turned into shared anticipation. Toby and Lennie cry over the scene he describes and kiss again; their grief briefly converges around Bailey’s imagined happiness, though that intimacy belongs to Lennie and Toby’s separate, painful entanglement rather than to Bailey and Toby’s partnership.

The ring and the unfinished announcement

Bailey’s grave eventually reveals a physical trace of the marriage they had not announced. When Lennie opens the small cabinet in the gravestone to place a notebook inside, she finds an orange-topaz ring, large as an acorn. She believes Toby must have had it made especially for Bailey and guesses that the ring was what they were waiting for before announcing their marriage and the baby. The discovery makes the unrealized news tangible: the ring was meant for Bailey to see and show off, but she never received it.

Lennie lays the ring on the stone, where sunlight throws amber-colored light across the engraved words, then later kisses it and returns it to the cabinet beside the notebook. This gesture does not complete the announcement or restore the future the ring represents. Instead, the object becomes part of Bailey’s memorial, held at the place Lennie chose for its closeness to the river. Toby’s gift, Bailey’s grave, and the words Lennie leaves there bring their private plans into the family’s continuing remembrance.

Significance of the relationship

Bailey and Toby’s story is framed by a striking movement from romantic spectacle to unfinished domestic possibility. Their first meeting arrives in Bailey’s imagination as an almost literary rescue on horseback; their later plans are more concrete, centered on a proposal, a ceremony at Flying Man’s, a pool, a ring, and an intended announcement about a baby. The shift shows the relationship becoming a future Bailey actively accepted and planned, even though Lennie had not known about it.

Because the narration reaches much of this future through Lennie’s bereavement, the couple’s happiness is repeatedly present as both remembered possibility and irreversible absence. Toby’s account lets Lennie picture the wedding, while the ring at the grave confirms how much of that plan remained unseen. Their relationship ends not through a choice to separate but through Bailey’s death, leaving Toby with a commitment still alive in hope and Lennie with the painful discovery that her sister’s life contained plans she can no longer ask about.