At 85 years old, Lillian traverses Manhattan on New Year's Eve 1984, wearing bright yellow tights, an emerald dress, a blue hat, and a prized mink coat bought in 1942. As a young woman in the 1930s, she moved to New York City and became the highest-paid female advertising copywriter in the country at R.H. Macy's, as well as a successful poet. She fiercely values her independence, prioritizes civility over unthinking politeness, and maintains a lifelong appreciation for clever wordplay. She often disregards societal expectations for women of her era, preferring to forge her own path.

Helen is a talented illustrator who becomes Lillian's roommate and closest confidant in New York City. She collaborates with Lillian professionally by creating the visual artwork that accompanies her advertising copy. Radiant, independent, and witty, Helen shares Lillian's early resistance to traditional marriage while experiencing the social freedoms of the city.

Max is a strong-jawed man with an eye for quality and design. He represents a major shift in Lillian's strictly independent lifestyle when she falls deeply in love with him. As her husband, he is initially progressive—supporting her career and sharing domestic duties—but his extended absences during World War II and subsequent government work alter the fabric of their marriage.

Lillian and Max's only child, whom Lillian affectionately nicknames Gian. Now an adult living away from the city, he worries constantly about his mother's safety in a changing, crime-ridden Manhattan and frequently urges her to relocate to Maine. His existence anchors Lillian to motherhood, an experience she views as both overwhelmingly emotional and inherently restrictive to her ambitions.

Lillian's boss at R.H. Macy's during the 1930s. He relies heavily on her exceptional copywriting skills to sell merchandise but actively upholds the era's patriarchal structures. He explicitly denies her equal pay by arguing that male employees need higher salaries to support their families, while Lillian is single.

A copywriter at Macy's who serves as Lillian's primary workplace rival. Olive writes traditional advertising copy steeped in sentimentalism and frequently criticizes Lillian's unconventional lifestyle. She conforms closely to societal expectations, actively hoping to find a husband, and attempts to emulate Lillian's success without possessing her creative talent.

Lillian's aunt, an independent woman who lived and worked in New York City. By sending her young niece rhyming advertising postcards, Sadie inadvertently shapes Lillian's future career path and provides a role model for a life outside traditional domesticity.

A highly educated woman who reads German fluently but married young and never worked for a wage. She views unconventional choices, particularly those of single career women, as a personal affront to her own domestic life, creating ongoing friction with her independent daughter.

An editor and publisher who believes in Lillian's literary talent enough to assemble her first book of poems. He respects her creative control but occasionally questions the cynical tone of her writing regarding romance, suggesting more upbeat titles.

The strict matron who runs the boarding house where Lillian and Helen live upon moving to New York. The young women must charm her and bend the truth in order to date men and stage theatrical productions under her roof.

An aspiring photographer living in a former Nabisco factory in the 1980s. She forms an intergenerational friendship with Lillian, appreciating the older woman's artistic perspective and eventually inviting her to a modern New Year's Eve gathering.

Wendy's partner, who lives with her in the converted biscuit factory. He appreciates Lillian's observant and nonjudgmental nature during her brief, overwhelming visit to their loud party.

The owner of a restaurant Lillian has frequented for years. He informs her of his plans to sell the business and move to Florida, prompting Lillian to feel a sudden sense of betrayal regarding the loss of her local community.

Max's second wife and Johnny's stepmother, who is fifteen years younger than Lillian. She is hospitalized with a severe heart condition during the modern timeline, prompting Johnny's anxious phone call.

A young clerk whose parents immigrated from the Philippines two decades prior. He works the night shift to give them a break and converses warmly with Lillian, selling her a potted amaryllis bulb instead of cut flowers so the gift will last longer.

A tall young man who demands money from Lillian during her late-night walk home. When he discovers she has given all her cash away, he negotiates a trade for her prized mink coat, demonstrating the unpredictable and slightly absurd nature of Manhattan.

A concerned limousine driver who worries about an elderly woman walking alone at night. He repeatedly offers Lillian a safe ride, proving that genuine kindness still exists on the gritty city streets.

A young expectant mother who worries about hospital staff judging her unmarried status. Lillian helps her handle the admission process, encouraging her to ignore societal expectations and focus on the future.