In the drama-filled season two premiere, an interview that Jill gave to the New York Post puts her in hot water with Alex and Simon. While on vacation in the Hamptons, Alex and Simon run into Jill at a party and their feud comes to a head. Bethenny decides to spend the summer with Jill at her Hamptons estate, and continue their whirlwind life on the social scene. Luann introduces new housewife Kelly Bensimon to the other ladies at a charity event.
Bethenny confides in Jill on the state of her relationship with boyfriend Jason, and Jill tries to help her out in her time of need. LuAnn, Bethenny, Ramona get together while Jill tries to get the "scoop" on new housewife Kelly, which sparks an argument with Ramona. While in the Hamptons, Alex and Simon engage in one of their favorite leisure activities - shopping! Jill's parents visit from Florida and while she is happy to see them, her mother is difficult to please. Meanwhile, Kelly receives VIP treatment when she shows up at a party that she is covering for work. LuAnn is being honored by The American Cancer Society and Bethenny and Jill attend to show their support. Also, Jill's mom bonds with Bethenny over her break-up woes.
Rosanna, LuAnn's housekeeper, joins the family again for a month-long trip to the Philippines. The entire family is thrilled to have her home, especially LuAnn, who has been doing a lot of extra work while she was away. LuAnn tells the other women that her daughter Victoria will be going off to boarding school in the summer, which causes an interesting reaction from one of the housewives. Jill decides to throw a major event for her charity, Creaky Joints, and plans to include the other housewives. Alex and Simon gets a luxurious spa treatment at their Hamptons rental home. Kelly competes in the esteemed Hamptons Classic, and Ramona stops by for support. LuAnn organizes a lunch for Victoria and her friends where she teaches them a lesson on etiquette. Bethenny, Jill and LuAnn attend the Hamptons Tea Dance, a major gay pride event of the summer. Meanwhile, Ramona's husband Mario decides to set up a tennis doubles re-match with Jill, and a disagreement ensues about who her partner should be.
The van Kempens return from the Hamptons to start packing for their annual vacation in St. Barts, while getting their house ready for a major home renovation. Jill begins a massive re-design of her entire home, with help from gay husband Brad. Bethenny does a photo shoot for Social Life magazine, and to her surprise, they decide to put her on the cover. LuAnn tells Bethenny that she is writing a book on manners and etiquette, though Bethenny disagrees on whether she is an expert on the topic. LuAnn organizes a charity event at Hope Lodge and invites Ramona, Bethenny and Jill to help out. During the event, Ramona and LuAnn butt heads over one of Ramona's "tell it like it is" remarks, and Bethenny gets upset by a comment that LuAnn makes about her Social Life magazine cover. At the Social Life party, the other Housewives come out to support Bethenny, but the comment that LuAnn made does not go unnoticed.
During one of the last weeks of summer, LuAnn is busy packing Victoria up for boarding school. Ramona and Bethenny get together in the Hamptons and dish over their recent arguments with LuAnn. Jill visits Alex and Simon at their home in Brooklyn to give them tips on renovation, and is shocked to see their house in its current state. Bethenny decides to clear the air with LuAnn and meets her for lunch, but the Countess doesn't take kindly to criticism.
It's fashion week in New York and the ladies schedules are jam-packed with invites to the Bryant Park tents. Jill and Bethenny go to lunch at Le Cirque where Bethenny talks about her dislike for Kelly. LuAnn, Kelly, Ramona and the van Kempens attend the Russell Simmons fashion show, where Ramona and Simon get into an argument. Jill has her first charity meeting for her "Creaky Joints" charity event, and Bethenny and Ramona attend. Kelly is busy covering fashion week for her Page Six Magazine column, and invites LuAnn to go shopping with her to find an outfit for the Malo fashion show. At the Jill Stuart show, Kelly is seated next to Bethenny, and tension ensues. Jill meets with designer Zang Toi, who is throwing a private fashion show for Jill and her friends, and he fits her for the perfect dress to wear the afternoon of the show. At Jill's next charity meeting, Kelly attends, but rubs everyone the wrong way.
Ramona invites Kelly to attend the Badgley Mischka fashion show together, where Kelly complains about Bethenny's behavior at Jill's charity meeting, and Ramona urges her to meet with Bethenny to talk it out. The two meet at a bar downtown, and the claws come out! All six of the Housewives attend the Page Six Magazine party, where Kelly talks to LuAnn about her fight with Bethenny. Mario approaches Jill about their upcoming tennis match, which turns into a very heated argument. Alex and Simon approach Ramona and Mario to clear the air over their long-standing feud, but things don't turn out as planned.
Jill's home re-design is finally complete, and she invites Bethenny over to see the results. While there, they learn that Jill's tennis pro won't be able to play with her in the doubles match against Ramona and Mario, so Bethenny suggest she ask Simon to play with her, which will definitely rub Ramona the wrong way. The other five Housewives attend the big match, and when Simon makes his grand entrance onto the tennis court, Ramona's reaction isn't exactly what Jill hoped for. Meanwhile, Bethenny asks Alex to help her design a logo for her line of "SkinnyGirl Margaritas."
Ramona is busy developing a skin care line, and decides to throw a party to show off the products. Bethenny attends and gives her advice on creating a brand, though Ramona isn't too eager to hear what she has to say. LuAnn meets with her writer to finish up her book, Class with the Countess, and also meets with her publisher to discuss how to market the book. Bethenny is out promoting her line of baked goods – Bethenny Bakes – in a store in Connecticut, but she finds it's not as easy as she thinks to give away free products. Kelly takes a trip out to LA to meet with a designer about her jewelry line. Simon plans something special for Alex's birthday, but loses his cool when the part of the surprise gets ruined.
Kelly goes to a sexy photo shoot to update her head shot and to shoot the photo for the invitation to the big Halloween party she is hosting. She decides to invite all the ladies to the party, even Bethenny. LuAnn's daughter Victoria comes home from boarding school for the weekend, and the two splurge on a shopping trip. Ramona is busy making a demo reel for her jewelry line that will be sold on HSN. Mario is shooting it and Avery is directing, but the tough critic that she is, Avery makes Ramona nervous and Ramona kicks her out of the room. Jill does an interview with BBC radio in her apartment on the topic of the American economy and how it's affecting wealthy New Yorkers like her. The van Kempens prepare for Halloween with their kids by carving pumpkins and decorating the stoop at their Brooklyn home. All the Housewives attend Kelly’s Halloween Party but much to their dismay, the drinks are served at a cash bar, the atmosphere isn't up to anyone's expectations, and most surprising of all, the hostess is missing.
Alex and Simon's home is in the final stages of the renovation, and they plan a party to show it off when it's finished and invite all the other Housewives. They discuss inviting everyone including Ramona and her husband, despite the rift between the two housewives. Bethenny gets set up on a blind date, and is nervous until she sees a photo of him and learns he's a model. She discusses her love life and plans with Jill, who is skeptical of Bethenny's confidence. Ramona is busy getting procedures done at her plastic surgeon's office and is amazed at all the new technologies that keep her from going under the knife. LuAnn's nieces are in town and Kelly is invited to go out with them for drinks; they are joined by Kelly's friend, Maximiliano. On the night of Alex and Simon's party, old grievances threaten to mar the new renovation.
Clashes, disagreements and conflicts abound as the ladies take care of the final details for Jill's charity event that they are all planning together. At the final charity meeting, Bethenny tries to patch things up with Kelly, and Ramona and Jill get into a fight. LuAnn's housekeeper Rosie wants Bethenny to teach her how to improve her cooking and Bethenny agrees to help. LuAnn uses her skills as a model to help Bethenny prepare for a fashion show. LuAnn and her husband get the opportunity to ring the NASDAQ bell together. Jill and Kelly run last minute errands together for the charity event, which doesn't make Bethenny happy. Some of the other Housewives show up to watch Bethenny strut the catwalk in the Moroccan fashion show, and Jill and Ramona decide to settle their differences about the charity event. On the day of the event, as expected Ramona ruffles Jill’s feathers, but everyone’s shocked when old allies start to fight.