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.

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.

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. Meanwhile, Ramona has a night on the town with her girlfriends, where multiple men try to pick them up at the bar. 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. They consider Jill a "connector" - and Jill relishes the role of being on the "inside" and introducing influential people to each other. At dinner, they also discuss their vacations to the Hamptons and St. Barts. LuAnn goes out downtown with her niece Nicole - her soulmate who "keeps her young". Rosanna stays home with Victoria and Noel to care for them and voices her opinion that the kids need more time with their parents. Bethenny meets her business partner Jake at a culinary event and networks with various movers and shakers in the food world. Over dinner, she talks about her absent father, troubled childhood and her desire to succeed despite him. Meanwhile, Ramona takes Avery to an audition for a Meryl Streep film. At the audition, she continues to coach Avery's acting, and the casting directors comment that they're unclear as to whether Avery wants it or is being pushed into acting. Bethenny and Jason plan a special, romantic dinner, and as a woman of action, she decides she is ready to officially move in together and springs the subject on him. Jason squashes the topic and leaves things unresolved.

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.

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 girl's 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.