A glittering Nantucket house party becomes a pressure cooker in Elin Hilderbrand’s The Five-Star Weekend, where one woman invites a single friend from each phase of her life to help her survive sudden loss. Over sunlit meals and stormy sails, old slights surface, secrets detonate, and the women test whether the bonds that shaped them can be remade. What begins as a curated weekend of comfort turns into a reckoning with identity, ambition, and the messiness of love.
Main Characters
Hollis Shaw
As the beloved food blogger behind “Hungry with Hollis” and the orchestrator of the Five-Star Weekend, Hollis Shaw arrives at the story’s center as a master hostess who can fix any problem but her own. Reeling from the sudden death of her husband, she masks grief and guilt—especially over their last conversation—beneath impeccable manners and control, a contrast established in the Prologue. Bringing together friends from her teens, college years, young motherhood, and midlife, she hopes for solace and instead confronts hard truths about her marriage to Matthew, her strained dynamic with Caroline, and her nostalgia for first love with Jack Finigan. Across clashes, confessions, and a devastating revelation about Gigi, the weekend becomes a crucible that burns away performance and points Hollis toward honest connection and a braver future, glimpsed in the Epilogue.
Tatum McKenzie
The Nantucket best friend who knows Hollis from summers and sandlots, Tatum McKenzie embodies island roots and the raw truth of who Hollis was before fame. Proud and razor-witted, she carries buried resentment—over class differences, over Hollis’s departure—and a long-standing rivalry with Dru-Ann, even as she remains fiercely loyal. Arriving with a private health scare and old hurts, Tatum’s prickly exterior dissolves through hard conversations and flashes of tenderness, including a cathartic sail on the Endeavor that helps her name and release decades of grievance (Chapter 41-45 Summary). By risking vulnerability with Hollis and Dru-Ann, she reclaims the steadiness of a friendship that once felt like family.
Dru-Ann Jones
A trailblazing sports agent who forged Hollis’s most formative collegiate bond, Dru-Ann Jones arrives at a professional and moral crossroads after a public takedown leaves her “canceled” (Chapter 6-10 Summary). Blunt, brilliant, and intimidating, she wears success like armor but reveals a deep capacity for loyalty—especially to Hollis and to her goddaughter, Caroline. Forced to operate far from press releases and power lunches, Dru-Ann collides with Tatum, listens harder than she speaks, and offers tough-love clarity that helps others stand taller. Her weekend reframes failure and redemption, mending a 25-year rift and renewing her sense of purpose.
Brooke Kirtley
Drawn from Hollis’s Wellesley “prime of life,” Brooke Kirtley begins as the overlooked mom-friend—eager, anxious, and aching for acceptance—whose husband’s serial misbehavior has eroded her confidence. Amid the glamour of the weekend, she expects to be the “fifth wheel,” yet finds allies who see her kindness and grit, especially in a burgeoning rapport with Dru-Ann. Encouraged to stop apologizing for other people’s choices, Brooke confronts her husband, claims her dignity (Chapter 26-30 Summary), and makes a profound discovery about her own identity that reframes her past and clarifies her future.
Gigi Ling
The elegant online friend from Hollis’s midlife audience, Gigi Ling enters as a poised confidante—and the weekend’s most compelling mystery. Gracious and magnetic, she carries the secret that she was Matthew’s mistress, a truth that binds her to Hollis by guilt and a fraught, almost anthropological curiosity. Her charm wins over the group, but a public ambush by Electra forces her duplicity into the open, detonating the weekend’s emotional climax at Galley Beach (Chapter 41-45 Summary). Gigi’s storyline wrestles with competing loyalties and the thorny question of whether empathy can coexist with betrayal.
Supporting Characters
Caroline Shaw-Madden
As Hollis’s daughter and the weekend’s videographer, Caroline Shaw-Madden is both observer and catalyst, her cynicism sharpened by grief for her father and anger at her mother’s public persona. Interviews with the “stars” complicate her judgments and expose hidden histories (Chapter 26-30 Summary), even as her affair with boss Isaac and a flirtation with Dylan underscore her own romantic confusion. The project becomes an unexpected bridge to reconciliation with Hollis.
Matthew Madden
A renowned cardiac surgeon memorialized as “Mr. Wonderful,” Matthew Madden exerts posthumous gravity, seen only through memory and revelation. As Hollis and Gigi’s recollections darken his halo, the discovery that he was driving home to reconcile when he died complicates easy condemnation (Chapter 46-50 Summary). He remains the absent presence whose contradictions spark the novel’s deepest questions about love and truth.
Jack Finigan
Hollis’s high school sweetheart, Jack Finigan represents the intoxicating path not taken and the steadiness of small-town devotion. His surprise return to the island stirs memory and desire (Chapter 11-15 Summary), culminating in a slow dance and a soul-baring talk in the Round Room that steadies Hollis’s heart (Chapter 36-40 Summary). In the Epilogue, he stands as a plausible, hopeful next chapter.
Electra Undergrove
Once part of Hollis and Brooke’s Wellesley circle, Electra Undergrove is the social climber turned saboteur who feeds on status and spectacle. Her cruelty keeps Brooke small—until Electra’s dramatic crash of the Galley lunch exposes Gigi’s secret and sparks the weekend’s turning point (Chapter 41-45 Summary). She is the antagonist who weaponizes gossip to devastating effect.
Minor Characters
- Kyle McKenzie: Tatum’s steady, good-humored husband, a loyal friend to Jack and a quiet guardrail for Tatum’s bluntness.
- Dylan McKenzie: Tatum and Kyle’s son, a handsome young father whose easy charm leads to a brief flirtation with Caroline.
- Charlie Kirtley: Brooke’s husband, a serial boundary-crosser whose behavior fuels Brooke’s shame and isolation—and her resolve to leave.
- Isaac Opoku: Caroline’s award-winning documentarian boss, whose affair with her exposes the cost of being someone’s second choice.
- Sofia Desmione: Isaac’s supermodel girlfriend, whose return to New York ends the affair and forces Caroline to face herself.
- Henrietta: Hollis’s Serbian sheepdog; her wary response to Gigi offers a subtle, canine chorus of doubt.
Character Relationships & Dynamics
The Five-Star Weekend pivots on Hollis and her “stars,” with each friendship illuminating a different self she has been. With Tatum, she shares a sister-deep bond strained by distance and class, the kind of love that can hold both ferocity and forgiveness. With Dru-Ann, she has a partnership forged in ambition and candor; they recognize each other’s drive and show up when reputations crumble. With Brooke, she plays mentor and protector, learning to see beyond neediness to a friend’s quiet courage. And with Gigi, she faces the raw edge of betrayal—an intimacy built on lies that turns into a confrontation neither woman can avoid.
Rivalries sharpen the weekend’s edges. Tatum and Dru-Ann’s 25-year tug-of-war for primacy in Hollis’s life, fueled by insecurity and class friction, resolves only when both risk vulnerability. Brooke’s long-standing fear of Electra—queen bee cruelty versus the perennial target—culminates in a public humiliation that, paradoxically, frees Brooke to choose herself.
Family threads cinch the emotional core. Hollis and Caroline, fractured by grief and mutual misunderstanding, move from guarded detente to tenderness as Caroline’s camera records stories her mother never told. Around them, informal factions form—the Nantucket locals (Tatum, Kyle, Jack), the Wellesley set (Brooke, Electra), and the high-powered world Dru-Ann represents—each exerting its own gravitational pull as the women decide which loyalties to keep and which performances to shed.
Character Themes
- Identity and Self-Discovery: Each woman confronts the gap between her public self and private truth—Hollis’s curated perfection, Brooke’s emerging sexuality, Dru-Ann’s recalibrated ambition.
- Authenticity vs. Public Persona: The weekend strips away branding and bravado; Hollis’s “Hungry with Hollis” and Dru-Ann’s cancellation test whether image can survive reality.
- Friendship and Its Evolution: Bonds stretch across decades and roles, proving that different seasons of life ask for different kinds of friends—and forgiveness.
- Secrets and Betrayal: Hidden affairs, private health fears, career crises, and closeted truths drive conflict and, ultimately, catharsis.
- Grief, Loss, and Healing: Framed by Hollis’s mourning, the novel becomes a collective ritual of letting go—of a spouse, a story about oneself, or a friendship stuck in the past.