What This Theme Explores
Past vs. Present in The Five-Star Weekend probes how memory, loss, and old loyalties continue to script the choices people make now. For Hollis Shaw, the ache of a romanticized marriage collides with what actually happened, forcing her to decide whether the past is a refuge or a distortion. The novel asks whether revisiting earlier selves brings clarity or merely reopens wounds—and whether reconciliation means restoring what was or accepting its limits. Ultimately, it tests if embracing one’s whole history can make the present more honest rather than more haunted.
How It Develops
The weekend begins as a controlled experiment in nostalgia. Reeling from Matthew’s death and his final, destabilizing judgment—“You’ve changed. And we’ve changed” (Prologue)—Hollis invites friends from distinct eras to make sense of her fractured now. The plan is part memorial, part pilgrimage: if she can assemble former versions of herself in one place, perhaps the present will stop feeling so unmoored.
The middle of the novel turns that nostalgia into confrontation. Old resentments surge the moment Tatum McKenzie and Dru-Ann Jones share a room again, their long-dormant feud coloring every exchange (Chapter 21-25 Summary). Then Hollis’s first love, Jack Finigan, steps out of memory and into the weekend, reanimating the gravitational pull of a different life she might have had (Chapter 11-15 Summary). The island becomes a theater where curated reminiscing gives way to raw, contemporary stakes.
By the end, the story reframes looking back as a means to move forward. Tatum and Dru-Ann finally name and dismantle the injury that has defined them during a hard-won conversation on the Endeavor (Chapter 41-45 Summary). Hollis shares a luminous, backward-glancing evening with Jack but recognizes that tenderness for the past is not a blueprint for the future (Chapter 36-40 Summary). In the Epilogue, the group’s recalibrated bonds suggest that integrating—rather than idealizing or repressing—the past yields a steadier present.
Key Examples
-
Hollis’s conflicting memories of Matthew: She clings to the gentle husband who built a Giverny-style bridge while also remembering the distance and the punitive final words that preceded his death. The mismatch between what she wants to remember and what is true sharpens her grief, showing how selective nostalgia can obstruct healing.
-
The return of Jack Finigan: Jack is memory made flesh, inviting Hollis to reinhabit the version of herself who once belonged to him. Their visit to the Round Room and a dance to “Wild Horses” suspend time, demonstrating how sensory cues can briefly eclipse the present—until the spell fades and the costs of living backward become evident.
“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.” “Of course I thought about you, Holly. You’re a part of who I am.” This exchange affirms that the past is indelible, but not necessarily directive: what remains is formative, not determinative.
-
Tatum’s grudge against Dru-Ann: Injuries from Hollis’s bachelorette and wedding metastasize into years of suspicion and scorekeeping. Their defensiveness—each convinced the other stole Hollis, status, or possibility—shows how unexamined slights can calcify into identity, until naming them frees both women from inherited postures.
-
Hollis’s Nantucket identity shift: The “local” girl who once lived in a modest cottage has become the polished “summer person,” a transformation that Tatum views with both pride and resentment. When Tatum texts, “You have officially become a Summer Person, Holly. Just like you always wanted,” the jab captures how place and class histories continue to script present belonging.
Character Connections
Hollis Shaw is the novel’s hinge between timelines. She designs the weekend to gather her former selves—girlfriend, wife, friend, island girl—believing the “real” Hollis might emerge from the chorus. Her arc accepts a more complicated truth: she is not one essential self recovered from the past but a composite who must carry love and regret forward without letting either define her limits.
Tatum McKenzie embodies fidelity to origins. Her rootedness in the old Nantucket—work boots, winters, and continuity—makes her wary of the glossier present. Opposite her, Dru-Ann Jones represents professional reinvention and mobility; their clash dramatizes the fear that change equals betrayal. Their eventual détente reframes change as evolution rather than abandonment.
Caroline Shaw-Madden initially mythologizes the past with her father and resents her mother’s branded, public-facing present. Hearing from Tatum and Dru-Ann about Hollis’s former hardships complicates Caroline’s narrative; empathy becomes possible when the past stops being a fairy tale and becomes a history with costs.
Brooke Kirtley remains trapped in a recent humiliation, excluded by Electra Undergrove. With Dru-Ann’s frank support, Brooke stops rehearsing that injury and claims a different social present, illustrating that agency often begins where nostalgia’s reruns end.
Symbolic Elements
The Twist, the repurposed guesthouse that was once Hollis’s modest childhood home, materializes the theme: the past can be preserved without being frozen, sheltering new life while honoring old foundations.
The curated playlists—’80s for Tatum, ’90s for Dru-Ann—are emotional time machines. They collapse years in a chord, showing how art reactivates memory and how quickly sentiment can overtake, and sometimes cloud, present judgment.
The Round Room is a shrine to first love. Returning there grants Hollis and Jack temporary asylum from adulthood, but its sacredness also underscores that some spaces are meant to be visited, not inhabited.
Nantucket itself splits into two palimpsests: the working-class island that formed Hollis and Tatum, and the luxury destination that now defines Hollis’s lifestyle. Their friction turns geography into biography, making place a ledger of who belongs—and who has changed.
Contemporary Relevance
In a world where old selves are archived across social media, the past is never out of reach—and never neutral. Hollis’s quiet stalking of Jack online reflects a broader impulse to verify what might have been, confusing curiosity with longing. The novel suggests that reconnection can be restorative when it is used to tell the truth about who we were and what we survived, rather than to cosplay a former life. The Five-Star Weekend models a ritual many crave: revisiting our histories not to rewind them, but to recontextualize them so the present can be lived less defensively.
Essential Quote
“You’ve changed. And we’ve changed.”
Spoken in the prologue, Matthew’s line is both accusation and diagnosis, distilling the novel’s central tension: is change a betrayal of the past or the only honest response to time? The story answers by showing that acknowledging change—between people, places, and selves—is painful but necessary work if the past is to enrich, not eclipse, the present.