In the first episode of "The Real Housewives of New York City," Ramona gets ready to go to the Hamptons for the summer with her daughter Avery, who thinks her mother should dress "more conservatively." At a pool party with her friends, Ramona "embarrasses" Avery by how she acts around her friends. Jill's daughter Allyson wants to go to a swanky detox center in Martha's Vineyard to work on her health and fitness, so Jill convinces Bobby to hire a private plane to take them there. LuAnn packs up her family and moves into their Hamptons home for the summer, with help from Rosanna, their housekeeper. They buy son Noel a puppy, but Rosanna is afraid that she will be the one who ends up taking care of it. Bethenny works on building her career, but is really focused on settling down with her boyfriend Jason. She wants to get married and have a child, but is afraid that Jason doesn't want the same things as he already has three children. Alex and Simon head to St. Barts for summer vacation, bypassing the Hamptons because vacationing there is "too much like work." They leave the kids at the hotel with their Au Pair and go on a glamorous shopping spree at Roberto Cavalli.

Jill and Allyson head to the detox center in Martha's Vineyard. Bobby decides to come along for moral support, which makes Jill extremely happy, but she finds it hard to leave Allyson there. Ramona gets ready for a fashion show in the Hamptons, and Mario and Avery help her find an "appropriate" outfit. Avery insists on a more "modest" looking choice, but Ramona sneaks out of the house with a forbidden top to change into. After she sees a young girl flirting with him, Ramona notices that Mario isn't wearing his wedding ring at the party. LuAnn's daughter Victoria, an accomplished equestrian, competes in the prestigious Hamptons Classic. Ramona brings her daughter Avery to the horse show, and they bump into Jill, who has also come to cheer on Victoria. Bethenny meets with fashion designer Ginny Hilfiger who is dressing her for Jason's sister's charity event, where she is auctioning off a personal cooking lesson. She has a meeting with her friend Jake, to discuss her business plans and how she wants to build her brand to become the next Martha Stewart. Back in the Hamptons, feelings and egos are bruised when Ramona throws a cooking party for several ladies and invites LuAnn but not Jill. Jill invites LuAnn to be her doubles partner in her big tennis match against Ramona at the end of the summer, and things get heated as they duke it out on the tennis court, leaving spectators to wonder if there was something more going on than just a friendly match.

Jill takes Allyson on a tiring back-to-school shopping trip at an expensive Manhattan boutique, where she notes that it costs "$1 million dollars" to raise a child in the city.LuAnn and Jill take their daughters to a Seventeen Magazine party so that Victoria can spend some time with Allyson, as they attend the same school. Ramona attends a Fashion Week show, where she bumps into Jill. Tensions rise when Jill realizes that Ramona is seated in the front row and she isn't. Ramona's daughter Avery is interested in getting into acting, so Ramona takes her to a prestigious modeling agency to see if they will work with her. Ramona is thrilled when the agency decides to send her out on shoots as they think she has "great potential," but Avery and Mario are concerned that it might take away from her schooling.Alex discusses how she and Simon first met and the challenges of raising children in New York City, namely, getting them into the right school. Alex and Simon present Francois with a new backpack for his first day of pre-k. Jill, Bethenny and Brad, Jill's "gay husband," go out on shopping trip, but Bethenny is embarrassed by Brad's "over-the-top" behavior. Jill takes her mother shopping and discusses her problems with Ramona. Her mother gives her a hard time about her clothing choices as she models them for her, but Jill just says it is just "constructive criticism."LuAnn and Ramona go to an Alice & Olivia fashion show, where Ramona states loudly that "models don't use their brains," embarrassing LuAnn, who is a former model herself.

Jill, Bethenny, Alex and LuAnn get together at a swanky New York restaurant. LuAnn and Alex hit it off, while Bethenny gets annoyed with what she perceives as Alex's pretentious behavior. Alex and Simon have dinner with Jill and Bobby, who have offered to help them get their son Francois into a private school through Jill's connections. Bethenny and Jason plan a romantic dinner, and as a woman of action, she decides she is ready to officially move in together and springs the subject on him. Meanwhile, Ramona takes Avery to an audition for a Meryl Streep film.

Bethenny meets Alex to teach her healthy cooking techniques for her family. Alex senses that something is wrong and Bethenny confides in her that she and Jason are having trouble, talking about her desire to have a baby and Jason's lack of commitment. Bethenny plans a trip to Miami to clear her head, and while she's out, gets a phone call from Simon inviting her to a surprise birthday party for Alex that night. The van Kempens get ready for their big night out. Simon blindfolds Alex and takes her to a yacht filled with all of their friends for a surprise birthday party. After everyone departs, Alex and Simon take a romantic sail around the Statue of Liberty. Ramona gets Avery and her friends ready for a school dance, where she reminds them that they have a lot of friends and should not be concerned with having boyfriends yet. She also reminds Avery that she'll be chaperoning at the dance, and Avery lays down the ground rules - Ramona is not allowed to talk to Avery or dance and embarrass her. Jill goes to Bethenny's apartment to help her pack for Miami, and they discuss Bethenny's baggage from previous relationships and her problems with Jason. Jill voices her opinion that Jason isn't perfect either, and they discuss what Bethenny might be able to do to salvage the relationship.

LuAnn has Bethenny over to her house for drinks, where Bethenny gets her opinion on her relationship with Jason. The two are getting ready to head to a restaurant for dinner and LuAnn's son, Noel, gets upset his mother is going out again. In the car on the way to the restaurant, LuAnn teaches Bethenny some rules in etiquette and how to deal with hired help. At a suite at the Hotel Chandler, Alex and Simon get made up for opening night at the opera, their biggest event of the year. Simon talks about how important an event like this is for their society connections. Jill and Bobby go out to dinner with Bethenny and Jason. Bethenny talks about the upcoming dinner party and Jill insists it be at her apartment. Bethenny warns them not to discuss babies or relationships in front of Jason, who is an hour and a half late for dinner and then decides to leave early. Meanwhile, Bethenny and Jill's "gay husband" Brad are at Jill's apartment getting ready for the dinner party. They have invited Alex who insisted on bringing Simon, despite it being a girls-only night and tempers flare as Ramona berates Alex for bringing Simon to a girls' night. After dinner, everyone is stunned as Ramona bursts out of the room and declares that she is leaving to go have a real girls' night out on the town. At a Habitat for Humanity charity event, Bethenny and Alex discuss what Ramona's real issues might be after her behavior at the dinner.