Gracefully Grayson (2014) is American teacher and author Ami Polonsky’s first book. (This guide is based on the 2016 Kindle edition.) This middle-grade novel uses realistic fiction to tell the story of a young transgender protagonist, Grayson Sender, as she deals with school life, relationships, and identity. Additionally, Gracefully Grayson explores the themes of Gender as a Societal Construct, Self-Identity Versus Perception, and Allyship as Empathy and Support. Due to its inclusion of LGBTQ+ topics in children’s literature, Polonsky’s novel was nominated in the 2015 Cooperative Children’s Book Center Choices List and the 2016 American Library Association Rainbow List.

Please note that, although the novel uses he/him pronouns to indicate that Grayson is perceived as a boy by other characters, this guide uses she/her pronouns to reflect her gender identity.

Plot Summary

The story is narrated by Grayson Sender, a sixth-grader who lives in Chicago with her Aunt Sally, Uncle Evan, and cousins Jack and Brett. Her parents died when she was four. Grayson is perceived as a boy by everyone around her, but she knows that she is really a girl. She likes drawing princesses and often imagines herself wearing dresses, but she is afraid of other people’s reactions should they find out who she is.

At school, Grayson usually keeps to herself, but when a new student named Amelia befriends her, she decides to open up. She shares her love of thrift stores with Amelia, although she looks longingly at other girls’ clothes but never dares to pick any for herself. Grayson and Amelia’s friendship develops as they are paired up in Mr. Finnegan’s class. Mr. Finnegan, or Finn, is Grayson’s favorite teacher and the school theater director.

When Amelia strikes up a friendship with another girl in the class, Grayson feels abandoned. Feeling like she is “disappearing,” she stumbles upon a flyer advertising auditions for the school play. She impulsively signs up and learns that the play that year will be the story of Persephone. Persephone is an ancient Greek goddess who was kidnapped by the god Hades and sequestered in the Underworld. Her mother Demeter, the goddess of harvests, let the crops die in despair, until Zeus, king of the gods, bargained for Persephone’s return. In the end, Zeus and Hades decided that Persephone would spend half the year above ground and the other half in the Underworld. According to mythology, this is what created the seasons, as every year the crops would grow for six months and then wither the next six.

In the audition, Grayson unexpectedly wants to read for the role of Persephone. Finn and Ms. Landen, another teacher, are surprised but encourage her to do so. When Grayson comes home, her aunt and uncle give her some letters they found in her grandmother’s old boxes. They are from Lindy, Grayson’s mother, and reveal that she and her husband knew about Grayson being a girl. Shocked by the revelation that her parents knew about her, Grayson falls ill and dreams of her mother. When she wakes up, she stares at the only thing she has left of Lindy, a painting of a phoenix. She learns that, while she was unconscious, Finn called to offer her the role of Persephone.

Uncle Evan and Aunt Sally are supportive of Grayson, but Sally feels like Finn should not have made the decision to cast her without consulting them. She is afraid that being seen as a girl onstage will open Grayson up to being bullied, so she reports Finn to the school principal. In the next few weeks, rehearsals begin, and Grayson falls in love with the world of theater. She befriends some of her cast members, in particular an older girl named Paige who takes her under her wing. Meanwhile, rumors about the consequences of the casting start spreading at school, and Grayson notices that Finn is avoiding her.

During rehearsal one day, Finn asks his students to reflect on what they know about their character, and Grayson realizes that what she knows about herself is that she is a girl. Later, she starts wearing girls’ clothes under her regular hoodie and lets some of the other girls from her class braid her hair playfully.

At home, Grayson’s relationship with her aunt is still tense. Eventually, Finn explains that he will leave the school at the end of the year but tells Grayson that she did nothing wrong. During dress rehearsal, Grayson takes off her hoodie, and Finn smiles at her when he sees her pink shirt underneath. Marla, Paige’s mother, helps sew the play’s costumes and lets Grayson know that she is always welcome at their house.

On the day of the play, Ryan, Grayson’s main bully, teams up with Grayson’s cousin Jack to attack her. She runs away but has a bad fall and breaks her arm. At the hospital, Sally is upset that Grayson chooses a pink cast, but Evan lets her pick what she wants. Grayson insists that she has to be able to perform that night, and she ends up doing a great job as Persephone. After the play, Finn leaves the school and sends Grayson a letter to say goodbye and wish her well. When his replacement asks the class what it means to be brave, one of Grayson’s former bullies replies that it means “there’s something important you have to do and you’re scared, but you do it anyway” (195).

Grayson excuses herself to go to the bathroom, where she takes off her girls’ shirt to put it over her regular one, puts hair clips in her hair, and goes back to class.