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 home with their Au Pair and go on a glamorous shopping spree at Roberto Cavalli.

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, so she decides to leave the event. 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. The agency decides to send her out on shoots as they think she has "great potential," but Ramona and Mario are concerned that it might take away from her schooling. Alex discusses how she and Simon first met and her thoughts on appropriate child-rearing techniques for their children. Her son Francois is getting ready to go to pre-k, so she and Simon go school shopping for a new backpack. Jill, Bethenny and Brad, Jill's "gay husband," go out on shopping trip, but Bethenny is embarrassed by Brad's "over-the-top" behavior. Also, Jill meets her mother for another day of 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.