As graduation day arrives at Ally and Jaime's High School, the only care in the world for these seniors is getting a hold of that diploma. That is, unless you are Ally Hilfiger and Jaime Gleicher. The topic of conversation with these stylish girls is how Jaime had, "The best shoes up there," and Ally's unbearably frizzy hair! Nonetheless, they both graduated with honors and are now ready to move on to the real world.
That is of course, after they celebrate at Gabriele's Restaurant where Ally and Jaime's families mostly discuss whether or not to eat the skin on their salmon. Ally's father decides to donate money to charity for her graduation present, but not before he throws her a graduation party at the Hilfiger home in Connecticut--a party (and a home) that most people can only dream of.
As the saga continues when Michael V. is a no-show at the girl's graduation and disappoints Jaime and Ally. Things seem to get worse when Michael V. decides to bring his girlfriend, Julia to Ally's party. Jaime seeks comfort among friends and Ally's best friend Ari who Jaime describes as, "genuine and kind, and who hates Mike."
As the night progresses, Ally learns much about herself from some informative psychics, while Jaime observes Michael becoming a little too "touchy feely" with just about every girl at the party--every girl but her. Michael barely knows what he has gotten himself into, because once Jaime's mom and Aunt notice how upset Jaime is, there's hell to pay. After a brief, yet threatening conversation with Jaime's family, Michael breaks down into tears. With Ally mediating, there is some hope of saving the devastated friendship between Michael and Jaime. But this all ends when Jaime overhears Mike calling her "jealous" of him and his girlfriend.
What a night! The girls decide they need a break from all the drama. So where do Rich Girls go to escape everyday life? The Hilfiger estate in the British West Indies, of course! Jaime is now beginning to shed that insecure persona, and is now becoming an independent woman as she is "detoxing from Mike." As the girls sit by the pool and discuss how fortunate they are, they question whether or not they deserve this privileged life. Ally and Jaime finally conclude that in their past lives they did something amazing, and are now privileged due to those past lives. Ally decides she was a tree, and Jaime ponders whether she could have been Benjamin Franklin.