Lily Jo McGrother is a thirteen-year-old trans girl in Beckford Palms, Florida whose classmates still think of her as a boy named Tim. Dunkin Dorfman is a boy with bipolar disorder. When Dunkin and his mom leave New Jersey to move in with Dunkin's grandmother in Beckford Palms, he and Lily meet and become friends.
Lily and Dunkin contains examples of:
- The Benchwarmer: Dunkin makes the basketball team because he's so tall, even though he's not a very good player. Coach Ochoa keeps him benched most of the time, only bringing him out to intimidate the opposing team.
- Bread, Eggs, Breaded Eggs: Before Dunkin's first basketball game at school, he worries about everything that could go wrong: he could trip, fall, miss the basket, or trip and fall while missing the basket.
- Childhood Memory Demolition Team: Lily learns that her favorite banyan tree, Bob, is due to be chopped down to make room for a playground. Lily puts a sign on the site urging people to protest and writes a letter to the mayor. When that doesn't work, she spends a day and a night tree-sitting. To no avail. Bob is chopped down.
- Christmas Creep: Lily's best friend Dare complains about seeing a flyer for the eighth grade holiday dance in December when it's not even Halloween yet. She grumbles, "There should be a law against advertising holiday stuff this early."
- Dramatic Drop: Last year Lily's Grandmom Ruth saw her walk down the stairs wearing a dress. She dropped a glass jar of strawberry jam all over the floor. She hasn't visited since.
- Embarrassing First Name: Dunkin is teased for his real name, Norbert.
- Exhausted Eye Bags: Dunkin's mom has dark circles under her eyes when she visits him in the hospital after his psychotic break.
- First Friend: Lily is the first real friend Dunkin has ever had.
- Freudian Excuse: Jerk Jock Johnny Vasquez, leader of the Gang of Bullies that is most of the basketball team, has a Sports Dad who screams at him in front of his teammates when he doesn't play well. He takes out his frustrations by harassing and assaulting Lily.
- Gym Class Hell: Lily does everything she can to avoid being in the locker room at the same time as Vasquez, who calls her "Fag!" every time he sees her, sometimes slams her head into the locker, and even yanks her shorts down in front of his friends to see if she's "really" a girl.
- Imaginary Friend: Dunkin's best friend from New Jersey, Phineas, turns out to be a hallucination who reappears when he goes off his meds.
- Is the Answer to This Question "Yes"?: Lily asks Dare if she's going trick-or-treating this year. Dare says, "Does a dog sniff another dog's butt to say hello?"
- Line-of-Sight Name: When Dunkin introduces himself to Lily, he's afraid she'll make fun of his name. Before he can tell her what it is, Lily says, "Dunkin," and points to the Dunkin' Donuts bag he's carrying.
- No Medication for Me:
- Dunkin's dad has bipolar disorder as well. The last time he went unmedicated, he decided to become the Denture King of South Jersey and spent all the family's savings on a billboard. Then he committed suicide. That's the reason Dunkin and his mom had to move to Florida. When they passed the billboard on the highway, Dunkin's mom flipped it off.
- When Dunkin accidentally skips a dose, he finds that his basketball skills improve. He decides to start intermittently skipping doses. His behavior becomes more and more erratic until he has a psychotic break on the basketball court and is carted off in handcuffs. In the mental hospital, he decides never to go off his meds again.
- Only Friend: Before Lily and Dunkin met, Lily's only friend was Dare, her best friend from preschool.
- Own Goal: During his manic episode, Dunkin makes a basket for the other team.
- Passing Notes in Class: On the first day of eighth grade, Lily passes Dunkin a note that says, "Hi, Dunkin!"
- Playing Sick: Faking a stomachache is one of Lily's tricks for avoiding Vasquez in the locker room.
- Secret Handshake: Lily and Dare have a secret handshake they created in fourth grade.
- Significant Name Shift: At the beginning of the book, Lily is delighted when her mom finally calls her by her name instead of Tim.
- Spiteful Spit: Vasquez spits on Lily when she wears nail polish to school.
- Switching P.O.V.: Lily and Dunkin both narrate.
- Trademark Favorite Food: Lily's favorite food is Pop-Tarts, which she eats with every meal.
- Why Couldn't You Be Different?: Lily's dad is the least accepting member of her family. He feels like if he lets her transition, he'd be letting his "son" die. He eventually consents for her to take hormone blockers after the doctor tells him about the suicide statistics for trans kids, and how kids who are supported by their families have a much lower risk.
