The Five-Star Weekend Summary, Characters and Themes

The Five-Star Weekend is a novel by Elin Hilderbrand. 

The story follows Hollis Shaw, a recently widowed food blogger who invites four friends from different stages of her life to her Nantucket home for a “Five-Star Weekend.” The weekend is meant to be a celebration of friendship, but old tensions, unexpected guests, and hidden secrets quickly surface.

Summary

Hollis Shaw, a renowned food blogger, is struggling to navigate life after the sudden death of her husband, Matthew. In an effort to find solace and reconnect with herself, she decides to host a “five-star weekend” at her home in Nantucket, inviting four friends from different stages of her life.

She hopes the gathering will allow her to rekindle lost connections while finding some comfort in the company of women who have each played a role in shaping her journey.

Her daughter, Caroline, a film student, is tasked with documenting the weekend, expecting to capture beautiful meals and picturesque scenes for her mother’s brand.

However, as the days unfold, Caroline discovers that the weekend is much more than a showcase of gourmet dishes; it becomes a window into her mother’s grief and the complex web of female friendships and forgiveness.

Among the guests is Tatum, Hollis’s childhood friend, who arrives carrying the heavy burden of anxiety over a recent breast biopsy.

Dru-Ann, a high-profile sports agent, is facing a personal crisis after a video of her goes viral, threatening her professional reputation and stability. Brooke, a mother reeling from her husband’s infidelity, seeks clarity and support from the group as she contemplates the future of her marriage.

Gigi, an online friend Hollis met through shared grief, joins them as well, hiding the painful secret that she once had an affair with Matthew, a truth unknown to the others.

As the weekend progresses, old wounds resurface and new tensions arise, especially with the unexpected arrival of Hollis’s ex-boyfriend, Jack, and the intrusion of Electra, a former friend who reveals Gigi’s affair with Matthew to the entire group.

This revelation forces Hollis to confront the betrayal head-on, leading to a tearful but ultimately forgiving resolution between her and Gigi, allowing both women to release the guilt and anger that had been holding them back.

Throughout the weekend, Caroline begins to see her mother not just as a grieving widow but as a woman who is deeply human, grappling with loss while trying to maintain her place in a world that demands her to be strong.

Tatum and Hollis find a way back to each other, rebuilding their childhood bond, while Tatum chooses to forgive Dru-Ann for past conflicts that had kept them apart. Dru-Ann faces her public crisis with newfound integrity and honesty, emerging from the experience stronger and more grounded in her values.

Supported by the love and encouragement of her friends, Brooke decides to leave her unfaithful husband and embrace her sexuality, choosing a life of honesty and freedom over silent suffering.

The weekend, intended as a time of connection, becomes a transformative journey for each woman, allowing them to confront the truths they have hidden from themselves and each other.

They later travel to Rome together, solidifying the bonds formed and healed over the weekend, their friendship deeper and stronger as they share laughter and understanding under the Roman sky.

On their flight home, ready to return to their lives with renewed purpose, they are comforted by a familiar voice over the intercom.

It is Gigi, now their pilot, guiding them safely back, symbolizing the forgiveness, growth, and resilience each woman has found, bringing the journey full circle as they move forward with hope and newfound peace.

Characters

Hollis Shaw

Hollis is a well-known food blogger and the protagonist of the story. She is recently widowed and grieving the loss of her husband, Matthew. 

Hollis organizes a “Five-Star Weekend” to reconnect with four friends from different stages of her life, seeking solace and comfort in their companionship. 

She is depicted as warm, welcoming, and passionate about food and friendship. However, beneath her cheerful facade, she grapples with grief, loneliness, and insecurity.

Caroline Madden

Caroline is Hollis’s daughter, an aspiring filmmaker studying at New York University. She is initially hesitant about her mother’s Five-Star Weekend, viewing it as a frivolous distraction from their shared grief. 

As the weekend unfolds, she becomes more involved in documenting the events, discovering hidden tensions and unexpected developments among the guests. 

Caroline’s perspective provides insight into Hollis’s character and the complexities of their mother-daughter relationship.

Tatum McKenzie

Tatum is Hollis’s childhood friend who is facing a health scare. 

She is awaiting the results of a breast biopsy, which adds a layer of anxiety to her weekend experience. Tatum is portrayed as loyal and caring, deeply valuing her friendship with Hollis. 

However, old tensions and misunderstandings from their past resurface during the weekend, challenging their bond.

Dru-Ann Jones

Dru-Ann is a successful sports agent and television personality, dealing with a public relations crisis that threatens her career. 

She is depicted as confident, ambitious, and sometimes blunt. Dru-Ann’s interactions with the other women, particularly Tatum, reveal a complicated history of rivalry and resentment. 

Her journey during the weekend involves confronting her past mistakes and seeking forgiveness.

Brooke Kirtley

Brooke is Hollis’s friend from their time raising children together. She is struggling with her husband’s infidelity and the unraveling of her marriage. 

Brooke is portrayed as kind, compassionate, and supportive of her friends. As the weekend progresses, she confronts her marital issues and explores a new path of self-discovery.

Gigi Ling

Gigi is a newcomer to the group, having connected with Hollis through her food blog. She is an airline pilot with a mysterious past. 

Gigi’s presence adds an element of intrigue to the story, as her connection to Hollis and her hidden secrets gradually come to light.

Jack Finigan

Jack is Hollis’s former high school sweetheart, who unexpectedly shows up during the weekend. 

His presence stirs up old feelings and memories for Hollis, complicating her journey of healing and moving forward.

Electra Undergrove

Electra is a former friend of Hollis and Brooke, who arrives uninvited to the Five-Star Weekend. 

She brings with her a secret that could potentially disrupt the fragile peace among the friends. Electra’s presence adds a layer of drama and conflict to the story, forcing the characters to confront unresolved issues from their past.

Themes

The Importance of a Multifaceted Identity

In The Five-Star Weekend, Elin Hilderbrand explores the multifaceted nature of identity through the character of Hollis Shaw. 

As a successful food blogger, Hollis is known for her curated online persona, showcasing a seemingly perfect life. However, the death of her husband reveals the cracks beneath the surface, exposing her vulnerabilities and struggles with grief. 

Throughout the weekend, Hollis navigates her various roles as a mother, friend, widow, and public figure, highlighting the complexity of human identity. 

The novel emphasizes that individuals are not defined by a single role but rather by a collection of experiences, relationships, and passions that shape their unique identities.

Growth and Forgiveness in Relationships

Hilderbrand delves into the complexities of female friendships and the transformative power of growth and forgiveness in relationships. 

Each of Hollis’s friends arrives on Nantucket with their own personal burdens and conflicts. Through shared experiences, open communication, and a willingness to confront past hurts, the women learn to forgive each other and themselves. 

The novel illustrates that relationships are not static but rather evolve over time, requiring understanding, compassion, and a willingness to embrace change. 

The characters’ individual journeys of growth and forgiveness ultimately strengthen their bonds, reinforcing the importance of supportive and meaningful connections in navigating life’s challenges.

The Supportive Nature of Friendship

The Five-Star Weekend underscores the importance of friendship as a source of support and solace during challenging times. 

Hollis’s carefully curated weekend is meant to be a celebration of friendship, but it quickly evolves into a space for vulnerability, honesty, and healing. As the women share their burdens and fears, they find comfort and strength in each other’s presence. 

The novel showcases the different ways friends can offer support, whether through listening, advice, or simply being present. 

Ultimately, the supportive nature of friendship emerges as a central theme, illustrating the profound impact genuine connections can have on individual well-being and resilience.

The Complexities of Grief

Hilderbrand explores the complexities of grief through Hollis’s journey of mourning the loss of her husband. 

Hollis’s grief manifests in various ways, from denial and anger to guilt and profound sadness. The novel does not shy away from portraying the messy and unpredictable nature of grief, highlighting its impact on Hollis’s relationships and daily life. 

Through her interactions with her friends and daughter, Hollis gradually learns to confront her pain, accept her loss, and find ways to move forward. 

The novel’s portrayal of grief serves as a reminder that healing is not a linear process but rather a complex journey that requires time, support, and self-compassion.

Embracing Change and New Beginnings

The Five-Star Weekend emphasizes that change, though often painful, is essential for growth and new beginnings.

Each woman arrives on Nantucket at a crossroads in her life, facing uncertainty, loss, or fear of the future.

Hollis is learning to live without Matthew while redefining who she is beyond her curated public image.

Brooke is forced to reimagine her life beyond a marriage that no longer serves her, while Dru-Ann must find a way to rebuild her reputation and trust in herself.

Caroline, witnessing the women’s struggles and resilience, gains a deeper understanding of how adulthood is filled with shifts that demand adaptability.

The weekend, therefore, becomes a symbol of transformation, illustrating how embracing change—rather than resisting it—can open the door to unexpected possibilities and self-discovery.

The Power of Vulnerability

Throughout the novel, vulnerability emerges as a powerful force for connection and healing.

Hollis’s willingness to invite women from different parts of her life into one space requires courage, as it means exposing her grief and imperfections.

The other women, too, are challenged to share their private struggles: Tatum’s health fears, Dru-Ann’s professional downfall, Brooke’s heartbreak, and Gigi’s shame and guilt over her affair with Matthew.

It is only through allowing themselves to be seen in their rawest, most honest states that they find understanding and support from one another.

The novel underscores that vulnerability is not weakness but rather a pathway to authentic relationships and emotional freedom.

Healing often begins when one has the courage to let others witness their pain.