The Five-Star Weekend

Caroline confides in Dru-Ann that she aspires to make a more serious documentary while working with Isaac. Dru-Ann catches Caroline’s admiring tone when she speaks about Isaac, and Caroline confesses to having an affair with him. Dru-Ann is familiar with Isaac, his work, and his girlfriend. She consoles Caroline, agreeing to answer questions about Hollis and help Caroline with her documentary.

Dru-Ann arrived at UNC expecting Hollis to be just as wealthy and privileged as Dru-Ann, so she was surprised at Hollis’s humbler background. The girls become close friends while rushing a sorority together. When Dru-Ann realized the sorority sisters believed Hollis was not wealthy enough to join their ranks, Dru-Ann persuaded Hollis to abandon Greek life and enjoy their friendship. By senior year, Hollis and Dru-Ann cultivated an inseparable friendship.

The only fight Dru-Ann recalls from their college years occurred when Dru-Ann discovered Hollis lied about her mother’s death. Dru-Ann believed Hollis’s mother was alive and well until she listened to Hollis’s phone conversation with Tom. Although hurt, Dru-Ann understood Hollis’s reason for lying and sympathized with her perspective. The experience drew the women even closer.

This story touches Caroline emotionally, who cries while seeing her mother in a new light. Knowing Hollis grew up without a mother, Caroline feels more appreciative of Hollis’s unwavering support over the years. While feeling sentimental remembering the tremendous effort Hollis put toward being a mother, Caroline’s phone rings—Isaac is calling.

Hollis lays out an immaculate appetizer selection for happy hour. She takes pictures for Hungry With Hollis, but she feels apathetic in doing so. She drinks a glass of wine while getting dressed for the evening. Defeated, Hollis wants to dismiss her guests. She believes Caroline was right to say Hollis is overly concerned with appearances. She regrets the time she poured into her work instead of focusing on her marriage.

Brooke wakes from a nap and cleans up in the beautiful outdoor shower. She tucks her phone away after seeing several abusive text messages from Charlie. Brooke feels self-conscious for a brief moment. Then, Gigi passes her as she exits the shower and asks Brooke to sit next to her at dinner. Immediately, Brooke returns to feeling happy and deserving of joy.

Tatum researches breast cancer on her cell phone. She feels overwhelmed by the various stages and many available treatments. Feeling terrified, she sends Kyle a picture of her dressed for dinner with a hint about which club the group plans on attending after dinner. Kyle replies lustfully, telling Tatum he plans on hunting her down before the club. Tatum smiles through tears.

Dru-Ann listens to several voicemail messages informing her of her termination from all jobs. She regrets knowing how little publicity and opportunity her current clients will now receive. Her neighbor and realtor calls to check in while inquiring about Dru-Ann’s apartment and if she plans on selling.

Isaac asks Caroline to lie to Sofia and reassure her that he remained faithful while Sofia was away. Caroline worries that Sofia knows about their affair, explaining her phone call earlier. Isaac reassures Caroline that Sofia suspects an affair, but not with Caroline; her earlier call was to inquire about female guests in Isaac’s apartment. Isaac tells Caroline he loves Sofia, but Caroline makes him very happy. Caroline feels too inexperienced with love to respond to Isaac’s comments.

When Isaac asks about Caroline’s “little project,” Caroline confesses to feeling a more meaningful story emerging. He agrees to review her footage together when she returns to New York. Sofia texts Caroline just as she hangs up the phone with Isaac.

Caroline admires the women dressed for dinner, realizing her mother’s color coordination plan works. The group wants to take a picture, but they all realize Hollis is missing. Caroline leaves to collect her mother. Walking to Hollis’s room, Caroline registers how horrible and selfish she acted toward her mother. For the first time, she thinks about what losing Matthew must have felt like from Hollis’s perspective. Knowing Hollis’s strain growing up without a mother, Caroline understands why her mother worked so hard to curate domestic perfection. Caroline deeply regrets hurting her mother.

Caroline finds Hollis in her underwear and crying. She runs to Hollis and apologizes profusely. Hollis feels as though she has her little girl back. Caroline distracts the other women while Hollis gets ready for dinner. They choose the best location for a group photo and swarm Caroline to see the shots. Caroline stays home from dinner to edit the images and footage, promising to meet the women at the club later. She genuinely wishes the women have a fun dinner together.

Another Nantucket resident, Sharon, and her sister gush over the gorgeous group of women as they arrive for dinner. They offer to take a group photo and express pride in Hollis’s glamour. After ordering appetizers and main dishes, Hollis toasts her friends for supporting her after Matthew’s death. The women reply with their love and appreciation for Hollis. Gigi asks Hollis to share the story of how she met Matthew.

Hollis remembers the incredible stage of life she experienced when she met Matthew. She loved her career working as a writer and editor for the foodie portion of a popular magazine. Her friend, Regency, suggested Hollis review a casual restaurant in Harvard as it was also a great place to meet male doctors. Hollis sat next to Matthew at random at the restaurant’s bar. Although he initially ignored Hollis, Matthew noticed her taking notes while enjoying her meal. He called her job “neat” when Hollis explained what she was doing. They enjoyed small talk for 30 minutes, and Matthew invited Hollis to a charity event at the hospital.

Hollis oversimplifies the growth of her and Matthew’s relationship while the five stars dig into their dinners. She recalls appreciating Matthew’s intellect, dancing moves, and kissing ability after the charity function. Soon after, Matthew invited Hollis to dinner with his parents in Wellesley, and she immediately warmed to his family. She tells her friends how thankful she feels for the beautiful life she and Matthew built together.

The rest of the five stars feel distracted by their hardships. Gigi has difficulty reconciling Matthew’s version of an unhappy, distanced marriage with Hollis’s more charming depiction. She asks Tatum about her career. When Dru-Ann and Brooke comment positively about Tatum’s job as a house cleaner, she asks the women not to patronize her. Hollis feels building tension among the group. She notices a woman in colors that match the group and is shocked to realize the woman is Electra.

Hollis ended her friendship with Electra five years prior because of the way Electra treated Brooke. Hollis admired Electra and loved her sense of humor, and becoming estranged hurt Hollis tremendously. She feels protective of Brooke, but Electra reveals that Brooke shared Hollis’s itinerary over drinks with Electra. Electra lies, telling Hollis that she and Brooke drank to their rekindled relationship. Brooke calls out Electra’s lies, standing up to her. Electra divulges Charlie’s sexual misconduct lawsuit to the group, and Brooke asks Electra to leave her alone. Hollis feels proud of Brooke but also betrayed that Brooke shared the weekend’s itinerary with Electra.

Electra stares straight at Gigi and says she knows her from somewhere else. Gigi looks panicked and denies ever meeting Electra. Dru-Ann notices the two young social media influencers arrive at the restaurant. Just then, Sharon grabs Electra by the arm, quietly threatening to have Electra permanently banned from Nantucket should she fail to leave the women alone. 

A sour mood falls over the group as Hollis pays for dinner. Gigi, Hollis, and Tatum declare they aren’t in the mood for a club. Gigi leaves the restaurant quickly, telling the others she will catch a taxi. Brooke believes the other women no longer want to be associated with her after hearing about Charlie’s misconduct. She relaxes when Dru-Ann agrees to go dancing with her. Tatum invites Hollis to a bar to meet Kyle and Jack for a drink. She hesitates, thinking of Matthew, but Tatum insists.

Hollis notices Jack’s handsome appearance and is glad she agreed to a drink with her old friend. She thinks back to junior prom, a perfect, beautiful, romantic evening. Hollis now regrets how badly she hurt Jack by breaking up with him. Tatum and Kyle leave for a drive, and Kyle promises to drop Tatum off later in the evening. Jack drives Hollis home, stopping in the same spot where they parked to fool around as teenagers. They talk, filling each other in on their life's happenings.

Hollis cries while confessing that the success of her website depends on her being strong, commanding, and decisive, all of which she does not feel. Jack comforts her, and Hollis divulges the discontent she and Matthew both felt before his death.

Hollis and Jack discuss a time they saw each other from a distance at a Nantucket Christmas tree lighting event 10 years prior. Hollis remembers feeling overwhelmed with emotion and a strong desire not to introduce Jack to Matthew and Caroline. She faked feeling ill to get out of dinner with her family to catch up with Jack. Jack recalls seeing Hollis look for him in the crowd but not wanting to interfere with her life. Hollis and Jack embrace and kiss, and Hollis realizes Matthew stopped kissing Hollis so passionately years ago. Jack and Hollis are interrupted by a police officer, Kevin, a friend from high school. They chat briefly, and Kevin apologizes for interrupting and leaves.

Caroline arrives at The Chicken Box, the club Hollis scheduled on the itinerary. Instead of seeing the five stars, she runs into Dylan. They get drinks together, and Dylan confesses he waited for Caroline to arrive. Caroline takes a few pictures with Dylan, posting them to her social media accounts, hoping they will make Isaac jealous.

Dylan and Caroline spot Dru-Ann and Brooke, and they take shots of tequila together. Brooke heads onto the dance floor, and the others follow after a few more tequila shots. They find Brooke dancing with a group of young men, and Dru-Ann pulls her away when the men make a sexually suggestive comment.

Dylan and Caroline dance, and Caroline takes several more pictures of them together. Dylan grabs Caroline and kisses her, and Caroline realizes how much she likes Dylan. However, Aubrey arrives and throws her drink in Caroline’s face. Dylan expresses outrage at Aubrey; Caroline calls Aubrey a “psycho” and leaves abruptly. 

While waiting for an Uber, Dru-Ann and Brooke grab a slice of pizza. Dru-Ann inquires about Charlie’s lawsuit, and Brooke starts crying. Brooke tells Dru-Ann about the past and present sexual misconduct cases. They both agree that Charlie is disgusting. Brooke tells Dru-Ann she believes Hollis hates her for leaking their itinerary to Electra, but Dru-Ann disagrees. Dru-Ann calls Brooke a “fun date,” and Brooke attempts to kiss Dru-Ann. Dru-Ann politely informs Brooke that she’s not romantically interested in women. They depart in an Uber.

Upon arriving at Hollis's house, Gigi heads to her bedroom. She knows Electra recognized Gigi as Matthew’s lover. Gigi packs her bags, feeling like she might need to make a quick getaway. She hears Hollis and Tatum arrive home, laughing and enjoying snacks. Gigi texts with her neighbor while Hollis tucks Tatum into bed. She feels unsure about what the events of the following day will bring.