CHARACTER
The Five-Star Weekendby Elin Hilderbrand

Brooke Kirtley

Brooke Kirtley

Quick Facts

  • Role: The “prime-of-life” friend invited to represent Hollis Shaw's Wellesley wife-and-mother era
  • Age/Background: Fifty-year-old mother of twins; suburban Wellesley socialite with a polished, preppy image
  • First Appearance: Introduced early in the weekend as Hollis’s hyper-loyal, eager-to-please friend
  • Key Relationships: Hollis; husband Charlie Kirtley; former friend Electra Undergrove; fellow guest Dru-Ann Jones; new acquaintance Gigi Ling
  • Thematic Arc: A late-in-life awakening centered on Identity and Self-Discovery

Who They Are

Brooke Kirtley wears perfection like a uniform: Lilly Pulitzer brights, a blowout to tame her curls, and a smile calibrated for social harmony. Beneath that sheen is a woman exhausted by keeping up appearances, terrified of exclusion, and trapped in a marriage that erodes her self-worth. She is loyal to Hollis and was a steady, practical presence after the death of Matthew Madden—the friend who shows up, organizes, and stays. Her self-stylized social persona even appears in images: beaming in a white LoveShackFancy dress, arms lifted in a triumphant V on a pristine bed. But the weekend strips the costume away. By confronting humiliation, desire, and truth, Brooke stops performing the role of “ideal Wellesley mom” and becomes someone real.

Personality & Traits

Brooke’s warmth and eagerness come with a cost: chronic second-guessing and a near-compulsive need to be liked. She overtalks to fill silence and stave off rejection, and she polices her body with the same vigilance she applies to her social life. Yet the very vulnerability she tries to hide becomes the engine of her transformation.

  • Insecure and approval-seeking: Ostracism by Electra’s circle haunts her; she monitors every interaction for slights and worries about being a “bother,” desperate to stay included.
  • Kind and steadfast: After Matthew’s death, she quietly handled logistics and offered emotional ballast for Hollis long after the casseroles stopped arriving—proof that her loyalty isn’t performative.
  • Talkative, over-eager, and nervy: Her anxious chatter—what Dru-Ann initially calls the “human equivalent of something stuck in your teeth”—masks a fear of abandonment and keeps people at arm’s length.
  • Unfulfilled in love and sex: Her marriage to Charlie is emotionally abusive and sexually barren, a truth she voices aloud at dinner, detonating the myth of their “perfect” home life.
  • Image-conscious and body-anxious: She counts calories, dons a rash guard at the beach, and straightens her curls—small acts revealing how control over appearance substitutes for a sense of self.

Character Journey

Brooke arrives on Nantucket defined by two wounds: the slow social death dealt by Electra’s exclusion and the private misery of her marriage to Charlie. The facade shatters when Charlie is publicly served for sexual misconduct and loses his job, forcing Brooke to face the truths she’s long minimized. A brief, manipulative “reunion” drink with Electra exposes Brooke’s relapse into old approval-seeking habits. But the weekend also delivers unexpected allies: when Charlie barges in drunk and abusive, Dru-Ann—once dismissive—defends Brooke fiercely, giving her a glimpse of what real protection feels like. Empowered by this solidarity and the weekend’s liberating friction, Brooke follows a spark of desire to its source: a spontaneous kiss with Dru-Ann that clarifies her sexuality. She experiments with honesty—first by telling a stranger, then by telling Hollis—that she is gay. By the weekend’s end, Brooke chooses herself: leaving Charlie, rejecting Wellesley’s petty hierarchies, and claiming a life that fits. The Epilogue confirms that choice holds—she’s thriving in a loving relationship with a woman.

Key Relationships

  • Hollis Shaw: Brooke adores Hollis’s poise and is deeply grateful to be chosen as a “prime-of-life” friend. She sometimes feels like a fifth wheel among Hollis’s other guests, but Hollis’s steady respect and inclusion give Brooke a safe place to be seen—first as the helper, then as her newly authentic self.
  • Charlie Kirtley: Charlie’s belligerence and serial misconduct isolate Brooke socially and erode her confidence. His public disgrace and drunken confrontation crystallize the truth: Brooke isn’t broken; the marriage is—and leaving him is the first real boundary she draws for herself.
  • Electra Undergrove: Electra is the queen bee whose approval once defined Brooke’s value. Their drink together triggers old patterns of neediness, but by weekend’s end Electra’s power over Brooke dissolves; Brooke no longer negotiates her worth with someone else’s gaze.
  • Dru-Ann Jones: What begins as irritation becomes respect, then desire, then catalytic honesty. Dru-Ann’s intervention during Charlie’s outburst models protective friendship—and their kiss jolts Brooke into recognizing her sexuality, transforming Dru-Ann from skeptic to unexpected midwife of Brooke’s becoming.
  • Gigi Ling: Gigi’s graciousness and elegance soothe Brooke’s social nerves. Feeling seen by Gigi offers Brooke a kinder mirror, helping her practice connection without performance.

Defining Moments

A weekend designed to celebrate Hollis becomes Brooke’s crucible—each shock burning off a layer of pretense until only the truth remains.

  • The Served Papers (Chapter 7): A deputy serves Charlie for sexual misconduct; soon after, he’s fired.
    • Why it matters: Public disgrace punctures Brooke’s denial and reframes her “marital problem” as systemic abuse and corruption she no longer has to excuse.
  • The Drink with Electra (Chapter 13): Electra coaxes Brooke into spilling details about the Five-Star Weekend.
    • Why it matters: The relapse into people-pleasing exposes Brooke’s core wound—an addiction to approval that she must break to become free.
  • The Dinner Confession (Chapter 17): Brooke blurts, “I’ve never had an orgasm with Charlie.”
    • Why it matters: Naming sexual emptiness converts private shame into shared truth, collapsing the fiction of her marriage’s normalcy.
  • Charlie’s Confrontation (Chapter 28): Charlie arrives drunk, insults Brooke, and is shut down by Dru-Ann and Hollis.
    • Why it matters: Witnessing herself defended—without her having to apologize or over-explain—recalibrates Brooke’s expectations of love and respect.
  • The Kiss (Chapter 39): In a parking lot after dancing, Brooke kisses Dru-Ann.
    • Why it matters: The moment converts vague discontent into specific desire, reorienting Brooke’s identity around what feels true rather than what looks right.
  • Coming Out (Chapters 44 & 51): She first tells the Endeavor’s first mate, “I’m gay,” then later comes out to Hollis.
    • Why it matters: Practicing truth in low- and high-stakes settings cements her new self, turning a private revelation into a public life.

Symbolism

Brooke embodies Authenticity vs. Public Persona. Her Wellesley-perfect wardrobe, controlled hair, and curated Instagram-ready smile mask a life of fear and deprivation. The weekend dismantles that costume. By abandoning the chase for approval and honoring her desires, Brooke proves that authenticity isn’t spontaneous—it’s chosen, practiced, and defended.

Essential Quotes

Brooke loves nothing more than to be included.
— Narrator, Chapter 2

This line distills Brooke’s core drive and her greatest vulnerability. Inclusion functions like oxygen for her, which makes her susceptible to manipulation—and makes her eventual refusal to seek approval a radical act of self-respect.

“I’ve never had an orgasm with Charlie,” Brooke says.
— Brooke, Chapter 17

The confession detonates the illusion of a functional marriage. By speaking body-truth aloud, Brooke shifts the conversation from appearances to reality, opening a door she can’t close again.

“I’m finished, Charlie. I’m done.”
— Brooke, Chapter 7

A line born in crisis becomes a boundary. Even if her resolve wavers after this moment, anchoring the words in public language helps Brooke eventually act on them.

Brooke is so happy, she nearly starts to cry. She’s glad the others aren’t around. Things always work out like they’re supposed to, she thinks; Brooke and Gigi were meant to have this time to bond.
— Narrator, Chapter 21

This tender interlude shows Brooke’s hunger to be chosen in small, private ways. Gigi’s warmth offers a corrective to Wellesley’s performative social scene, nudging Brooke toward relationships grounded in ease rather than status.

“I came out of my walk-in closet this weekend,” she says.
“I’m gay,” she says.
— Brooke, Chapter 44

The joke softens the vulnerability, but the truth lands with clarity. Turning identity into speech completes Brooke’s arc: from managing perception to declaring reality, she chooses a life that can hold her.