Toby is Bailey's boyfriend. As the novel begins, Toby is grieving and he turns to Lennon because she was close to Bailey and they are close to the same age. At first Lennon is surprised by this because Toby never seemed to notice her before. However, she soon finds herself a target for Toby's passions. As their relationship grows closer and more complicated, Lennon finds herself torn between the relief Toby offers for her grief and the lack of a true emotional connection between them. When Joe comes into the picture, Lennon is even more confused, a situation that grows even darker when Joe sees Toby and Lennon kissing. It is a difficult situation that Toby tries to help Lennon repair. In the end, Toby and Lennon know that they were only using one another to get over their grief and decide that a brother-sister relationship would be better for all concerned.