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.

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.