Hollis is a recently widowed food blogger from Nantucket who runs the successful website Hungry With Hollis. Striving to process her grief and jumpstart her content creation, she organizes an extravagant five-star weekend with friends from different stages of her life. She is a dedicated mother and professional, though her pursuit of domestic perfection sometimes alienates those closest to her.

Caroline is an NYU film student struggling with the sudden death of her father. She agrees to film her mother's weekend getaway in exchange for rent money, though she harbors resentment toward her mother's focus on her blog. Instead of capturing aesthetically pleasing content, she hopes to film a profound documentary focused on interpersonal conflict.

Tatum is Hollis's oldest friend, representing her childhood years on Nantucket. She works for an island cleaning service and feels disconnected from the wealthy status Hollis has achieved. She attends the weekend to distract herself while anxiously awaiting the results of a breast biopsy.

Dru-Ann is Hollis's best friend from their college years at the University of North Carolina. She works as a prominent sports television personality and agent for female athletes. A short video of her speaking harshly to a client's father goes viral, plunging her into a massive public relations crisis just as she arrives in Nantucket.

Brooke befriended Hollis during their early years of motherhood. She constantly seeks external validation, obsessing over social media likes while struggling with deep insecurities. She attempts to keep a cheerful demeanor while hiding that her husband faces a second lawsuit for workplace sexual misconduct.

Gigi is a commercial airline pilot who connects with Hollis over the Hungry With Hollis website. She serves as the representative for Hollis's midlife digital friendships. After providing emotional support following Matthew's death, she travels to Nantucket to meet Hollis in person for the first time.

Electra is a former close friend of Hollis and Brooke. After a mysterious falling out years prior, she feels excluded and harbors intense resentment toward the group. She attempts to insert herself into the five-star weekend to stir up drama and assert dominance.

Matthew is Hollis's late husband and a world-renowned cardiac surgeon. He struggled to support Hollis's growing success as a food blogger, creating emotional distance in their marriage. His sudden death serves as the primary catalyst for the weekend gathering.

Jack is Hollis's former high school boyfriend. He still resides in Nantucket and appears during the weekend, bringing up nostalgic memories of Hollis's younger, simpler life before she became a wealthy public figure.

Isaac is an established, 34-year-old filmmaker who mentors Caroline at NYU. He encourages her to seek out underlying conflict rather than shooting superficial content, though he occasionally acts dismissive of her project and feelings.

Kyle is Tatum's devoted husband. He has been with Tatum since their preteen years and serves as her primary emotional anchor while she navigates the anxiety surrounding her medical biopsy.

Charlie is Brooke's husband. He frequently belittles Brooke and isolates her socially. He faces severe professional and legal repercussions after inappropriately touching a young coworker.

Dylan is the adult son of Tatum and Kyle. He shares a brief romantic history with Caroline from their teenage years and reconnects with her when she returns to the island. He co-parents his toddler with his ex-girlfriend.

Posey is a professional golfer and one of Dru-Ann's clients. She decides to fake a mental health crisis to skip a tournament, prompting Dru-Ann's harsh lecture that ultimately goes viral and damages Dru-Ann's career.

Nick is Posey's father and Dru-Ann's romantic partner. He enables his daughter's poor professional behavior, leading to the argument that jeopardizes Dru-Ann's television career.