The Real Housewives of New York City (2008)

Brynn and Jessel catch up with Sai at a champagne play date in Brooklyn; Ubah and Erin dish over coffee in Washington Square Park; the ladies who find themselves caught in a web of rumors confront each other at style icon Jenna Lyons' girls night.

Erin hosts the group at her sprawling Hamptons home, but champagne and caviar leaves some of the ladies hangry for more. The women divulge personal details during dinner at Erin's favorite Hamptons hot spot, and Jessel reveals intimate information about her marriage. Luckily, Jenna has the perfect gift to spice things up.

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.

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.

Sai shares her content creation journey, and Jenna cleans out her multiple closets of fashion artifacts. Escalating tension between Erin and Jessel makes for a frosty café confrontation that Brynn and Sai hear about over a game of chess. Jessel hosts a charity event attended by the who's who of the fashion elite, except for Jenna Lyons.

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.

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.

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.

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.

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.

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.

Back in New York, Sai and Erin share a spicy double date with their husbands and Brynn plays wing woman to Jenna. Ubah hosts a post-Anguilla healing session for the group. Jessel finally has a staycation with her husband, but at lunch with Sai, she tests their friendship.

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.

Brynn celebrates her birthday and the masks come off as friendships and state lines are crossed.

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.

Tensions escalate as Sai opens up about her relationship with her mom. Brynn breaks down when sharing more about her childhood.