What This Theme Explores
Revisiting the Past in The Five-Star Weekend asks how memory can be both a sanctuary and a snare—and what happens when we drag it into daylight. For Hollis Shaw, looking back is not nostalgia; it is a deliberate excavation of the choices and friendships that shaped her. The novel tests whether old hurts can be reinterpreted without erasing their sting, and whether the self that once was can be reconciled with the self that now is. It ultimately explores how healing requires not a retreat into memory but an honest integration of it.
How It Develops
At the outset, grief cracks Hollis open. After her husband’s sudden death, she latches onto a Motherlode article and conceives a weekend that gathers one friend from each era of her life, as if building a living archive. Even before the guests arrive, her private backward gaze turns compulsive—she stalks Jack Finigan on Facebook, chasing a version of herself that existed with him, testing whether the past still answers.
When the women assemble, the past stops being an idea and starts throwing elbows. Old resentments—especially between Tatum McKenzie and Dru-Ann Jones—flare immediately, pulling everyone into the undertow of bachelorette-party slights and wedding-day hierarchies. The weekend’s activities become a crucible, exposing how much of the present is calcified by unexamined memories. Hollis’s imagined reunion with Jack, once a safe daydream, becomes a destabilizing reality that forces her to test fantasy against fact.
By the end, the deliberate return to former selves yields harder truths and gentler conclusions. Tatum and Dru-Ann finally articulate their competing narratives and uncurl the decades-long grudge, discovering that forgiveness is a future-facing act. Hollis revisits the Round Room with Jack to untangle first love from enduring love, and, in doing so, honors her marriage without denying her earlier longing. The Epilogue affirms that the past is neither buried nor boss—it is folded into the present with care, making room for change.
Key Examples
The weekend refracts the theme through staged events that keep slipping into unscripted reckonings, revealing how memory resists curation.
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The Conception of the Weekend: Hollis designs a gathering that is essentially a time capsule turned inside out. By inviting one friend from each life chapter, she constructs a living timeline that can question her current identity. The choice frames the narrative as an experiment: what happens when the past is given a seat at the present table?
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The Resurfacing of Old Conflicts: The Tatum–Dru-Ann feud reignites the moment they share space, and Tatum’s rubber-snake prank exposes how easily old roles reclaim people. This regression reveals that unprocessed history keeps emotions adolescent, no matter how adult the participants. Their spiral demonstrates the cost of leaving the past unspoken—resentment traps them in time.
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Jack Finigan’s Return: Jack’s arrival collapses Hollis’s private nostalgia into a testable proposition. Their conversation in the Round Room forces Hollis to confront the gap between mythologized first love and the flawed, breathing person before her. The encounter reframes her marriage not as a compromise but as a distinct, completed chapter that can be honored alongside earlier desire.
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Caroline’s Interviews: As the group’s filmmaker, Caroline Shaw-Madden turns reminiscence into testimony by asking each woman to narrate her history aloud. When she prompts Tatum, Dru-Ann, and Brooke Kirtley, their on-camera answers provide competing “archives” that expose memory’s subjectivity. The lens forces precision, making the past accountable to language rather than to haze.
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Recreating Past Moments: When Hollis and Tatum dance to “Take My Breath Away,” muscle memory becomes emotional memory. The routine resurrects a younger confidence and intimacy, reminding them that joy, too, is part of their shared past. The moment suggests that revisiting earlier selves can be restorative rather than regressive.
Character Connections
Hollis Shaw carries the theme’s moral weight. As curator and subject, she wants the past to offer solace without complication, but the weekend teaches her that solace requires friction. By confronting her mother’s absence, Jack’s hold on her imagination, and the fractures among her friends, she learns that reconciliation is not erasure; it is synthesis.
Tatum McKenzie embodies a hometown past that feels abandoned. Her resentment toward Hollis for leaving Nantucket and toward Dru-Ann for “replacing” her reveals how loyalty, unacknowledged, curdles into grievance. Tatum’s arc—naming the hurt, hearing its mirror, and letting it loosen—shows that revisiting the past is a way to stop reliving it.
Dru-Ann Jones represents Hollis’s aspirational reinvention. Her competitiveness and defensiveness trace back to a younger insecurity, and facing Tatum pushes her to admit what that ambition cost. By acknowledging that her ascent was shadowed by fear, she transforms the past from a pedestal into a lesson.
Jack Finigan personifies the seductive “what if.” His presence tests whether a first love is an origin story or a destination. Hollis’s willingness to meet the real Jack—not the curated highlight reel—lets her honor who she was without mistaking it for who she must be.
Symbolic Elements
The Twist: The childhood cottage, moved and modernized into a guest space, literalizes the book’s thesis—keep the structure of the past, but change how you inhabit it. It’s not demolished; it’s repurposed, proving that history can be preserved without being a prison.
The Round Room: This clearing, once a site of teenage initiation, becomes the stage for adult reckoning. Returning there reframes the memory through mature eyes, illustrating that place can remain constant even as meaning evolves.
The Playlists: Era-specific songs operate as time machines that bypass rational defenses. Because music collapses time emotionally, the playlists expose how quickly the past can flood the present—and how sensory memory can be harnessed for connection rather than escape.
The Five-Star Weekend Itinerary: Hollis’s meticulous schedule symbolizes the fantasy that the past can be safely curated. Yet the most transformative moments occur off-script, revealing that healing thrives in unpredictability, not control.
Contemporary Relevance
In a world where social media makes yesterday perpetually clickable, the novel interrogates the difference between scrolling through memory and sitting with it. Hollis’s initial Facebook “stalking” is familiar and frictionless; the weekend forces the messier work of context, conversation, and contradiction. The book suggests that while digital nostalgia can spark curiosity, only embodied encounters—awkward, unscheduled, and sincere—can untangle the knots that curated feeds conceal. Revisiting the past, done bravely, becomes a tool for accountability and renewal.
Essential Quote
“I wanted to know if you were still with her,” Hollis says. “I guess what I really wanted to know was if you ever thought about me.”
This confession distills the theme’s core tension: the desire to confirm that the past still matters—and thus that we still matter within it. Hollis’s need for acknowledgment exposes how memory is relational, not solitary; its power depends on being mirrored. The moment transforms nostalgia into dialogue, enabling Hollis to reframe longing as understanding.