Tensions escalate as Sai opens up about her relationship with her mom. Brynn breaks down when sharing more about her childhood.
Brynn tells about her fears on motherhood. Ubah accuses Jenna of being two-faced. Erin and Sai get to the root of their ongoing squabbles. Jessel takes the women to task for speculating about her marriage.
Brynn celebrates her birthday and the masks come off as friendships and state lines are crossed.
Couples' night, hosted by Erin and her husband, puts Jessel and her husband in the hot seat. Ubah shares a secret with Sai. Jenna takes her son shopping. Sai shares a heartwarming moment with her aunt.
On the group's final day in Anguilla, a storm moves in over Erin and Ubah's friendship. The women venture out for a rum tour where Sai revives her bartending career. The ladies limbo with the locals, but Erin leaves early. Jessel's hit list is revealed. At the villa, Erin seeks resolution but is boiled in the hot tub instead.
Erin catches Brynn up on the newest tension between Sai and Jessel. During the group's picture-perfect boat day, Jessel clashes with Erin and Sai while Brynn and Jenna get closer than ever. Back at the villa, Ubah and Erin's pranks on each other result in a shocking shift in their friendship.
In Anguilla, Jenna continues to open up to the group and Sai gets surprisingly vulnerable. Jessel's story of her own upbringing causes confusion. The ladies beach and bond with a sun-soaked photoshoot, but when leaving lunch, Brynn finds herself on the defense again.
Over the holidays, Jenna's brother visits New York and Brynn connects with her brother in Los Angeles. Sai and Ubah shop for the group's warm-weather getaway to Anguilla, but Jenna's choice to fly separate from the rest of the ladies results in an icy greeting on an island paradise.
Sai helps Jenna cast models for her false eyelash line. Brynn helps her ex-fiancé shop for luxury classic cars. After keeping her IVF journey a secret, Jessel finally reveals her infertility struggles to her mother. Brynn invites the women to holiday wreath making, where Erin confronts her about her antics.
Ubah takes Erin diamond shopping for her 10th anniversary party. Jessel navigates the exclusive New York City pre-school scene. At Erin and Abe's anniversary party, a bored Brynn stirs the pot and Sai gets upset about the lack of food.
Back in the city, Erin checks in on a renovation and Ubah consults her mentor for business advice; Jessel addresses intimacy issues with her husband and Jenna shares with Erin what Jessel really thought of the trip.
The women confront Jenna for sneaking out in the middle of the night. Brynn arrives in the Hamptons. At lunch, the women grill Jessel over her incessant complaining and Brynn calls out a double standard. Over sushi, everyone bonds playing a scandalous game of Two Truths and a Lie.