The Five-Star Weekend

The Five-Star Weekend is a realistic romance novel by best-selling American author Elin Hilderbrand. The author’s 29th book, The Five-Star Weekend explores Growth and Forgiveness in Relationships while navigating main character Hollis Shaw’s four closest female friendships during a girls’ weekend in Nantucket, Massachusetts. The novel topped several bestseller lists upon its 2023 release, including that of The New York Times.

This guide refers to the 2023 e-book edition published by Little, Brown and Company, a division of Hatchette Book Group.

Plot Summary

Hollis Shaw eagerly decides to host a five-star weekend in the wake of her husband’s death. Matthew Madden died in a car accident immediately after he and Hollis argued about their commitment to each other. Surrounding herself with her four best friends from four different stages of her life while indulging in lavish food, wine, and activities seems like a fitting way to battle Hollis’s intense grief. A famous food blogger, Hollis needs to jumpstart content creation for her website, Hungry With Hollis, after a seven-month hiatus. Hollis asks her daughter, Caroline Madden, a film student at New York University, to capture video and photo images of her weekend. Caroline and Hollis share a strained relationship after Matthew’s death. Initially feeling less important than Hungry With Hollis, Caroline learns to understand her mother’s roles and accept The Importance of a Multifaceted Identity.

Hollis invites Tatum McKenzie, a childhood friend; Dru-Ann Jones, a college friend; Brooke Kirtley, a motherhood friend; and Gigi Ling, a middle-aged friend, to her home in Squam, Nantucket. Although Hollis envisions the weekend to be relaxing, indulgent, and fun, each friend arrives in the middle of her own crisis. Tatum recently underwent a breast biopsy and nervously awaits the results. Dru-Ann, a well-known sports television personality and an agent for female athletes, is in a public relations crisis after a short, out-of-context video went viral depicting Dru-Ann criticizing a client’s mental health. Thousands are calling for Dru-Ann to be canceled. Brooke’s husband, Charlie, is being sued for sexual misconduct for the second time. Gigi, a Hungry With Hollis subscriber, plans to meet Hollis in person for the first time on this trip. Hollis and Gigi grew close via virtual communication, and Hollis found Gigi’s support after Matthew’s death invaluable. Gigi is a pilot, and while Hollis believes the women share no connection aside from a love for food, Gigi engaged in an affair with Matthew for nearly a year before his death.

Hollis wants Caroline to capture aesthetically pleasing footage of the extravagant food, drink, and Nantucket landscape her smiling, color-coordinated friends enjoy. However, Caroline aspires to make documentaries for a living and intends to create a more profound short film. Her mentor and ex-lover, Isaac Opoku, advises Caroline to seek out conflict while digging beneath the surface of her subjects. Luckily for Caroline, a dramatic weekend unfolds, made all the more emotional by the appearance of Jack Finigan, Hollis’s ex-high school boyfriend. Additionally, Electra Undergrove, Hollis and Brooke’s estranged friend from years prior, crashes Hollis’s five-star weekend and reveals Gigi’s relationship with Matthew.

Growth and Forgiveness in Relationships emerges as a central theme as each character’s conflict nears resolution. In hearing about Hollis from her mother’s close friends, Caroline gains diverse perspectives, affording her empathy and understanding of her mother’s motivations and grief. Tatum rebuilds her lost friendship with Hollis while forgiving Dru-Ann of long-past transgressions. In the end, the lump in her breast is a cyst. Dru-Ann’s integrity never breaks as she faces her public relations crisis. Dru-Ann and Tatum’s reconciliation demonstrates the power of growth and forgiveness in relationships. Brooke decides to divorce Charlie, and, through The Supportive Nature of Friendship, Brooke comes out as gay. Hollis confronts Gigi about her affair with Matthew in a private, emotional conversation that leads to Hollis’s forgiveness.

The novel closes with four couples (Hollis and Jack; Tatum and her husband, Kyle; Dru-Ann and her boyfriend, Nick; and Brooke and her girlfriend, Trinh) returning from a Rome vacation. The group hears Gigi’s voice over the airplane intercom, introducing herself as their pilot as they head home.