Laura Dean Keeps Breaking Up with Me (2019) is a graphic novel written by Mariko Tamaki and illustrated by Rosemary Valero-O’Connell. Tamaki is known for her critically acclaimed graphic novels and comics that often explore themes of identity, relationships, and coming of age, and this collaboration with Valero-O’Connell features young adult (YA) fiction with elements of LGBTQ+ romance and slice-of-life storytelling. Since its publication in 2019, Laura Dean Keeps Breaking Up with Me has garnered significant praise, winning the 2019 Harvey Award for Best Children’s or Young Adult Book and receiving nominations for the Ignatz Award and the Lambda Literary Award. The title reflects the central conflict of the story, as the protagonist, Freddy, navigates the ups and downs of her tumultuous relationship with Laura Dean. Through Freddy’s journey, the book explores themes of self-discovery, toxic relationships, and the importance of friendships, ultimately delivering a story of a teenager learning to prioritize her own well-being and finding her place in the world.

This study guide refers to the 2019 edition published by First Second Books.

Content Warning: The source text describes psychological manipulation and a sexual relationship between an adult man and a minor.

Plot Summary

The graphic novel’s 17-year-old protagonist, Freddy, grapples with the emotional turmoil of her on-again, off-again relationship with Laura Dean. In the opening pages, panels depicting Freddy and her friends at a school dance are juxtaposed with caption boxes in which Freddy narrates an email that she has addressed to an advice columnist named Anna Vice. Through these captions, Freddy reveals that Laura has broken up with her three times over the past year. At the dance, Freddy discovers Laura making out with another girl, which leaves Freddy devastated.

Freddy tries to cope with the heartbreak with the support of her friends Doodle, Eric, and Buddy. Despite her efforts to move on, Freddy finds herself drawn back to Laura when she receives a text from her. Seeking guidance, Freddy confides in Doodle, who introduces her to a mysterious figure known as “the Seek-Her,” a Dungeons and Dragons dungeon master renowned for her insightful advice and predictions. At The Door, the local gaming establishment, the Seek-Her listens to Freddy’s account of how Freddy and Laura fell in love during a square-dancing activity in gym class. The Seek-Her observes that Freddy is trapped in a “non-monogamous swing-your-partner wormhole” and advises her to break free from the cycle by ending her relationship with Laura (70). Feeling frustrated after her encounter with the Seek-Her, Freddy finds Laura waiting for her at home. The two of them end up having sex on Freddy’s bed. However, their time together is marked by Laura’s dismissive attitude toward Freddy’s interests and Laura’s abrupt departure, which leaves Freddy feeling uncertain and confused.

As Freddy navigates her feelings for Laura, she also engages in discussions about sex, intimacy, and consent with her friends Eric and Doodle, who are facing their own relationship challenges. Freddy’s friendship with Doodle becomes increasingly strained as Doodle grows unhappy about Freddy’s rekindled romance with Laura, culminating in Doodle secretly making plans to visit The Door without Freddy. Meanwhile, Freddy finds herself at a party at Laura’s house, feeling isolated and neglected as Laura flirts with another girl. As Freddy reflects on the nature of relationships and societal norms, she muses about the dynamics of relationships and the changing landscape of traditional family structures, drawing comparisons to her own family and those of her friends. She reflects on a TV show she watched that depicted polygamy, and she tries to draw connections between the logic of the show and her unclear relationship with Laura, telling herself that perhaps she needs to be more open-minded about relationships.

Freddy’s rekindled relationship with Laura continues to strain her friendships, particularly with Doodle. Despite feeling neglected by Laura, Freddy rationalizes their relationship in an email to Anna Vice. A series of panels depicts the growing distance between Freddy and her friends, while also hinting at Doodle’s life beyond her friendship with Freddy. Freddy meets Vi, a girl who works at the donut shop and bowling alley, who invites her to a gallery event. At the event, Freddy impulsively kisses Mo, Vi’s friend, after seeing Laura flirt with another girl. The next day, Laura confronts Freddy about the kiss but asserts that they will always get back together. Freddy agrees, neglecting her plans to meet Doodle for lunch. As Freddy spends more time with Laura, Doodle becomes increasingly distant, and Buddy chastises Freddy for not checking on Doodle, who has been absent from school.

In the concluding section of the novel, Freddy learns that her best friend Doodle is pregnant after sleeping with a married man she met at The Door. Despite tension between Freddy and Doodle, Freddy offers to accompany Doodle to her abortion appointment. However, Laura’s manipulative behavior causes Freddy to be late to the clinic. As Freddy comforts Doodle after the procedure, she reads an email response from Anna Vice; it encourages her to reflect on the nature of her love with Laura and whether it brings her happiness and personal growth. Inspired by this advice, Freddy gains the courage to break up with Laura, prioritizing her own well-being and her friendship with Doodle. The story concludes at prom, where Freddy celebrates her newfound independence and strengthened bond with Doodle. She is happy that she has chosen to be a good friend and is focusing on personal growth rather than defining herself through her relationship to Laura.