Lillian Boxfish Takes a Walk is a 2017 picaresque novel by Kathleen Rooney. The narrative is loosely based on the life of the American writer Margaret Fishback, reputed to be the highest-paid advertising woman in the world in the 1930s, who published well-received poems and short stories from that time until the 1960s. The reflective novel unfolds in the span of a single night—New Year's Eve 1984—and follows 85-year-old Lillian Boxfish as she takes a walk through Manhattan, encounters a vibrant cross-section of its inhabitants, and reminisces about her life, career, and the myriad changes she has witnessed in New York City over the decades. Through Lillian's eyes, Rooney explores the city's history, its highs and lows and infinite possibilities, and the evolution of women's roles in society.

This study guide uses the 2018 Picador Paperback edition.

Content Warning: The novel and study guide discuss pregnancy loss, racism, alcohol use disorder, suicide, mental health conditions, and anti-LGBTQ+ biases in connection with the HIV/AIDS epidemic of the 1980s.

Plot Summary

The novel moves backward and forward in time as Lillian recalls various aspects of her life and career. It begins with recollections of the postcards sent to Lillian by her Aunt Sadie. Lillian admires Sadie for being an independent woman in New York City, but Lillian’s mother disapproves of anyone who does not lead a conventional life. In present-tense 1984, Lillian receives a call from her son, Johnny, letting her know that his stepmother Julia is in the hospital about to die of a heart attack. He begs her to leave New York City because crime keeps getting worse, but Lillian insists that she will never leave and ends their conversation to prepare for her New Year’s Eve dinner at Grimaldi’s restaurant. The remainder of Lillian’s reflections occur while she is walking from one destination to the next.

She stops at a bar called the Back Porch and recalls 1931: She became the highest-paid female copywriter in America. However, the male copywriters still made more than her. After being profiled in a newspaper as the darling of the ad world, Lillian went to the office early to ask her boss, Chester Everett, for a raise. Her co-worker, Olive Dodd, was already there and enviously suggested that Lillian should be grateful for what she had. Lillian believed that Olive wrote inferior copy, but she did her best to temper her criticism. Chester apologized but explained that the men had families to support, while Lillian was single, so she was paid less. This was frustrating for Lillian, who saw the women around her as fixated on matrimony, while she was not interested in marriage.

Lillian’s first book of poems, Oh, Do Not Ask for Promises, was set to be published in 1932. Lillian walked to her publisher’s office to finalize the book plans, where her editor suggested that Lillian change the title of her collection to something more upbeat; Lillian firmly refused. The book became a major success, republished four times. At work, Chester asked her if she might be oversupplying her admirers with too much writing, but Lillian dismissed him. She went on to publish four more poetry collections.

Leaving the bar, Lillian decides to walk past the first place she lived after moving to New York City, and the novel flashes back to 1926. Lillian lived at the Christian Women’s Hotel with her best friend, Helen McGoldrick, who would later become as successful an illustrator as Lillian was a writer. The girls staged plays at the boarding house to make money, but they had to tell the strict matron who ran it that they were donating the money to charity. Helen and Lillian both had boyfriends they did not want to marry, though they enjoyed having sex with them. Both soon got jobs working for R. H. Macy’s and moved into an apartment together. They enjoyed the freedom that New York City offered them, which they knew they would not have elsewhere.

As Lillian continues her walk on New Year’s Eve, she visits Grimaldi’s, Madison Square Park, Delmonico’s Restaurant, and St. Vincent’s Hospital. In each place, she recalls and reveals more about her life and her eventual marriage to a man named Max Caputo.

In 1934, Lillian went to buy a rug for her new apartment and fell in love with the Macy’s rug-buyer at first sight. They married soon after, much to the amusement of people familiar with Lillian’s poetry and skepticism about love. Lillian wondered if she had made the right decision marrying Max. On the honeymoon, Max convinced Lillian to try living in the suburbs, but after a couple of unhappy months, they moved back to the city. They had their only child in 1942 after a series of pregnancy losses. Lillian had to leave her job because the agency did not offer maternity leave, but Chester promised that he would send her freelance work.

Max was drafted into World War II and was gone for two years. When he returned, he began working for the government and was often away. Lillian loved her son more deeply than she could have imagined, but she did not feel comfortable in her role as a mother and often longed for the life she once had. She became melancholy and misused alcohol. Eventually, Lillian learned that Max was having an affair with Julia, who was 15 years younger than her. On a cruise in 1955 intended to raise her spirits and help the couple patch things up, she attempted suicide. She was committed to a sanitarium where she received electric shock therapy. When she recovered, leaving the hospital as a newly divorced woman, Lillian felt that she had become everything she always hated.

Lillian continued her freelance work in advertising and adapted to a new life. In 1980, she was invited to appear on a public access program with two modern copywriters. The younger women disparaged Lillian’s style and she left the studio in disgust, thinking that modern advertising only appealed to people’s basest instincts and desires. Walking home through the city still comforted her, but she no longer ran into people whom she knew.

Back in 1984, Lillian decides on a whim to take up an invitation from a young photographer she has befriended, Wendy. She stops at a bodega to buy hostess gifts and goes to Wendy’s apartment, which is at the old National Biscuit Factory. Though Wendy and her friend Peter are gracious, some of the younger guests are rude, and Lillian does not want to be at the party when the clock strikes midnight. She sets out for home but is accosted by a group of young men who demand her money. Having spent or given away all her cash over the course of the night, she shocks the boys by offering a trade instead: her mink coat for one of their jackets. After a final stroll past RH Macy’s, Lillian returns home to her cat, Phoebe. Though she feels out of touch and lonely because of her age, many of her interactions have been interesting, and she reflects that she has been true to herself and will continue to stay interested in life.