Josie is the manager of Tabula Inscripta, an independent bookstore specializing in literary fiction and nonfiction. She is a meticulous, highly organized perfectionist who values intellect and order, using her bookstore as a safe haven from her chaotic past. After dropping out of college to care for her sister, Josie places immense pressure on herself to succeed professionally, making her fiercely competitive when her livelihood is threatened. She views romance fiction as unserious, which fuels her rivalry with the manager of the romance bookstore next door.

Ryan is the dedicated manager of Happy Endings, a bookstore devoted entirely to the romance genre. Having struggled with dyslexia and feelings of mediocrity in a family of overachievers, he finds profound purpose in helping readers see themselves in love stories. He inherited his passion for bookselling from a beloved mentor and actively champions the emotional value of romance novels. Though he creates a welcoming, slightly chaotic space for his customers, he harbors deep-seated insecurities about his own worthiness of love.

Georgia is Josie's younger sister, a graduate student studying psychology at Tufts University. She walks with a cane following a severe childhood accident that significantly altered both her and her sister's lives. Perceptive, optimistic, and unguarded, Georgia often acts as an emotional mirror for Josie, analyzing her sister's coping mechanisms and gently challenging her aversion to vulnerability.

Xander is a pragmatic real estate investor and businessman who owns the entire block housing Beans, Happy Endings, and Tabula Inscripta. Focused entirely on his bottom line, he approaches the local businesses with a profit-driven mindset. He announces the structural merger of the three shops and initiates the high-stakes competition, pitting the two bookstore managers against each other for a single remaining position.

Josie and Georgia's mother is a woman with a tumultuous romantic history that deeply affected her daughters' upbringing. During periods of heartbreak, she often retreated into romance novels, leading to severe neglect where young Josie was forced to act as the primary caregiver. Her ongoing search for love continues to be a source of tension and skepticism for her eldest daughter.

Cinderella is the assistant manager at Happy Endings romance bookstore. A middle-aged divorcée who adopted her unconventional name following her separation seven years prior, she is a dedicated and supportive presence in the store. She participates enthusiastically in the staff's brainstorming sessions and book discussions.

Nora is an elderly employee at Happy Endings. She brings a seasoned, mature perspective to the bookstore's staff meetings, openly discussing her literary preferences and critiquing the poor portrayal of older characters in fiction. She offers grounded advice when her colleagues face dilemmas.

Eliza is a high school student working at Happy Endings. She is an avid reader who critiques the tendency of young adult literature to simplify romantic content. She actively participates in the store's efforts to increase revenue during the competition.

Indira is a college student employed at Happy Endings. During staff meetings, she shares her specific reading preferences and helps the team brainstorm creative event ideas to keep the bookstore afloat during the high-stakes profit competition.

Eddie is the manager of Beans, the coffee shop located between Tabula Inscripta and Happy Endings. He is a friendly neighborhood presence who observes the ongoing rivalry between the two bookstore managers from behind the counter, occasionally offering advice or lending resources for their events.

Gretchen is a fellow romance bookseller and a friend of Ryan's. She is looking to open her own bookstore on the Cape and offers Ryan a backup employment plan in case he loses the managerial competition in Boston.

Penelope Adler-Wolf is the highly successful owner of Wolf Books in Providence, Rhode Island. She represents the pinnacle of literary bookselling success to Josie, who idolizes her and aspires to achieve a similar level of professional respect in the literary fiction community.

Kenneth Michael Rutherford is an international bestselling author whose debut novel was shortlisted for the National Book Award. His presence at Tabula Inscripta initially seems like a major win, until his controversial and problematic views are brought to light during his event.

Darrell is a doctor who becomes engaged to Josie and Georgia's mother. The couple plans a trip to Puerto Vallarta, Mexico. To Josie, Darrell represents yet another in a long line of her mother's fleeting romantic pursuits, while Georgia tries to see him as a sign of positive change.

Elaine is the deceased original owner of Happy Endings. Years ago, she caught a young Ryan attempting to shoplift and, instead of pressing charges, had him work off his debt by reading romance novels aloud to her parrot. She became an important mentor figure, introducing him to the bookselling trade.

JR was a close teenage friend of Ryan's who tragically passed away during their senior year of high school. Struggling with his family's rejection of his sexuality, JR's death deeply affected Ryan, inspiring him to curate a diverse romance collection so that all readers can see themselves in healthy relationships.

Brenda is the mother of Ryan's late friend, JR. She visits the bookstore for the first time in over a decade to buy an LGBT+ romance novel upon Ryan's recommendation, sharing a brief but warm reunion that reminds Ryan of the importance of his work.

John is Ryan's older brother. He is a successful lawyer who contributes to the high standards of achievement within the Lawson family, making Ryan feel ordinary by comparison.

Paul is one of Ryan's older brothers. Working as a surgeon, he adds to the family's pattern of high-achieving professionals.

Robert is Ryan's older brother, employed as a nuclear engineer. His impressive career path reinforces Ryan's lifelong insecurities about his own perceived mediocrity.

Ryan's mother is celebrating fifty years of marriage. Her seemingly perfect relationship sets an intimidating standard for romance that Ryan fears he can never replicate, though she holds a more realistic view of how her marriage succeeded.

Ryan's father is the patriarch of the Lawson family. He is celebrating fifty years of marriage, representing the kind of enduring romantic success that his youngest son finds daunting.