Lily and Dunkin by Donna Gephart was originally published in 2016. A coming-of-age novel set in contemporary America, the book tells the stories of two unique and inspiring teenagers who find themselves and each other. Lily and Dunkin was named one of NPR’s Best Kids’ Books of 2016, one of Amazon’s Top 20 Children’s Books of 2016, and one of YALSA’s picks for Best Fiction for Young Adults in 2017. This guide is based on the 2016 edition by Yearling, an imprint of Random House Children’s Books. 

Plot Summary

Lily Jo McGrother was born a boy named Tim, but she identifies as a girl. She has lived most of her life as Tim, presenting in public and at school as male. However, six days before eighth grade, she tries on her mother’s red dress and feels conflicted: part of her relishes being herself, and the other is terrified of others’ reactions. Daring to head outside, Lily waves to the cute new boy in town, even though her father is irate. Lily’s father struggles with Lily’s transgenderism, worried about violence and bullying. Lily hopes that she can convince her father to allow her to get hormone blockers and love her as the person she truly is.

Norbert Dorfman, a recent transplant from New Jersey to South Florida, is the boy who Lily waves at. Later, Lily climbs the banyan tree that she calls Bob, named after her Grandpop with whom Lily shared a close relationship. Norbert passes beneath the tree. Forgetting that she is now dressed as a boy, Lily jumps down and accompanies him to Dunkin’ Donuts. When Norbert inevitably asks about the dress, Lily lies, saying it was a dare. Norbert reveals he doesn’t like his name, and Lily suggests she call him Dunkin. Dunkin doesn’t reveal that he is medicated for bipolar disorder, that his father committed suicide due to the same illness, or that he imagines a person named Phineas when not medicated.

Despite encouragement from her best friend, Dare, to be herself at school, Lily dresses as Tim for the first day. Still, bully John Vasquez and his Neanderthal friends harass Lily, calling her a “fag.” Dunkin does nothing, hoping the bullies will leave him alone. When those same bullies include Dunkin socially, Dunkin is conflicted because of their cruelty, but decides he’ll do whatever it takes to fit in, including lying about his ability to play basketball and rejecting Lily. Dunkin starts to skip his bipolar medications, thinking it will improve his basketball skills. His behavior becomes increasingly erratic, including rapid speech, boundless energy, and poor sleeping habits. Later, Dunkin begins talking to himself at school and on the basketball court.

Lily’s parents take her to see a psychiatrist as the first step toward hormone blockers. The psychiatrist privately relates the suicide rate for transgender teens to Lily’s father, and he becomes more supportive. Lily begins painting her nails and wearing makeup at school, and the Neanderthals continue to bully her. When Lily goes out for Halloween dressed as a mermaid, her father expresses the danger in her actions, and Dunkin distracts the Neanderthals to protect her.

The city marks Lily’s tree, Bob, for removal. Lily climbs into his branches and refuses to leave when they come to cut him down. She settles in to sleep in Bob for what she knows will be his last night. Dunkin happens by and joins Lily in the tree; Lily shares her secret with Dunkin, and she is pleasantly surprised by his acceptance. Dunkin realizes that Lily is truly his friend. Dunkin has a bipolar episode and hallucinates on the court at a basketball game. After police forcibly remove him, Dunkin wakes in a mental health facility. As the medications start to work, Dunkin finally confronts the truth about his father’s suicide.

Vasquez and his friends violate Lily by pulling her pants down in the locker room. Ashamed, depressed, and feeling dirty, Lily avoids school for days. However, when the school dance arrives, Lily knows that she needs to be herself. With her mother, sister, and Dare by her side, Lily attends the school dance as Lily. Dunkin wonders whether he’s ready for the other kids to stare at him at the school dance. However, he knows that attending could save Lily from harassment. Dunkin reveals his illness and his father’s suicide to Lily. Dunkin and Lily dance the last dance, and Lily’s father arrives to show his overwhelming support for the daughter he loves.