Getting into the second half of The Five-Star Weekend, the series has reached a real fork in the road. Despite Hollis' best efforts to keep the weekend light and fun, the spa trip made sure to bring all of the low-simmering drama to the surface, including the unfortunate revelation that Hollis has continued to be friendly with Electra. How will she save the weekend now?
The Five-Star Weekend episode 5 kicks off with Hollis looking at an old recipe video social media post and reading all of the love in the comments. She takes a phone call from Chelsea, who applauds the content she has been posting from the weekend and gives her a pep talk for Saturday night's fancy dinner out. Ironically, Gigi has resolved to tell Hollis the truth about Matthew.
Brooke's phone call with Charlie leaves her even more confused about where she stands with everyone in her life, especially after he doesn't immediately refute her question about his allegations. Before heading out, Gigi tries to be honest with Hollis but chickens out. Brooke breaks the black and white outfit dress code and wears jeans and a green blouse.

A night at the bar brings fights, kisses, and tears
After seeing the group off on their tuk tuk ride into town, Caroline accepts Dylan's invitation to hang out later that night in spite of her plans to spend time with Aubrey. During dinner, the group senses tension between Brooke and Gigi, but Brooke steps in before Gigi can drop the Matthew bomb to confess about their kiss. The conversation turns to grief changing a person's identity.
Dru-Ann's boss calls her with the news that Posey has been caught lying about needing time off and partying while watching her boyfriend play. This twist will make Posey look bad and absolve Dru-Ann, but she feels conflicted about the turn of events. When Caroline meets Tyler at his waiter job, she has to wait for him a little longer and she's forced to wait outside by the hostess (played by Mamrie Hart!).
Brooke opens up about the possibility that she's attracted to women, and when Hollis returns to the table after meeting with the chef, she silences her friends when she says, "Work is all I have." Tatum notices her doctor across the way and looks like she's seen a ghost, but she doesn't approach him to ask about her results. She immediately proposes going out to get drunk for ladies' night at the local bar.
While out at the bar, Brooke dodges calls from her husband and takes her wedding ring off. Gigi's friend John Mark unexpectedly appears at the bar to stop Gigi from telling Hollis the truth. Hollis quickly learns from fans that Electra publicly shared the group's weekend itinerary. Dru-Ann gives Brooke the stern talk she needed to get her "out of her body" and talk to a woman.

Gigi writes a letter and Hollis falls apart
Tatum spirals over the fear she faces about her results, and Dru-Ann finally talks to Posey after seeing her onscreen partying at the Knicks game. She warns Posey that she can't be photographed at the game and has clearly chosen Posey's future over her own. Tatum confronts Hollis about sharing her medical situation with Dru-Ann and spills Caroline's secret, which wasn't hers to tell.
Back at home with John Mark, Gigi wrote Hollis a letter that confesses the truth about her relationship with Matthew. John Mark assures her that no matter what happens, telling the truth will absolve her of her guilt but won't ever allow her to be actual friends with Hollis. Brooke chats with the walking tour guide, Sunny, who likes that she talks too much and intently listens. They dance together.
Dru-Ann thought that Caroline was only taking a semester off of school not failing out. After hearing this, Hollis demands that Dru-Ann calls her so she can actually talk to her daughter. Hollis insists that she knows how Caroline feels, but Caroline breaks down about the possibility of Hollis moving on with a second marriage and never getting her father back. Dru-Ann ignores a call from Posey just after Hollis sternly bites back about Caroline calling to confide in her.
Dylan walks up to Caroline after she's been crying, and she doesn't take more than a second to decide to risk it and kiss him. They venture to the lighthouse to have sex, where they're caught by Officer Teddy. Jack picks Hollis up as she walks home in the street. They dance to "their song" in Hollis' driveway and finally get that kiss they almost had. During the kiss, she pictures Matthew. As Hollis emotionally breaks down in her room, Gigi rushes in to hold her.
Watch The Five-Star Weekend only on Peacock.
