Welcome to the life of two typical teenagers--Ally and Jaime. They live in Manhattan and go to ritzy private schools by day and lavish parties by night. They're best friends who "prance around the damn city like it's their shopping haven." Just like every other high school senior in America, they're preparing for prom. And just like some of us, Jaime is determined to loose her virginity on prom night. The lucky guy is Jaime's date Craig, ("nice open guy") whom she's been dating for a few weeks. Ally, on the other hand, doesn't have a date but is more than willing to be a "wallflower" for the evening. The girls go shopping to a special boutique where "regular people" aren't allowed, with Michael H., Ally's sort-of uncle. They have fun playing dress-up and find everything but a prom dress. The shopping continues and they take Fifth Avenue by storm.
Prom day arrives and the girls head to Frederic Fekkai salon to get prepped for the big night. While they get their hair styled, their friend Michael V. calls. He is the "Ryan Phillippe from Cruel Intentions" in their social circle. He doesn't think that they should split the cost of the limo for prom and it seems like Ally and Jaime will be paying for it by themselves. The girls aren't too happy about this but say that they have grown used to their people taking advantage of them. Over pedicures and coffee, they further discuss Jaime loosing the big V. Jaime told Craig what she wanted to do but from his reaction, he might not be ready for such a big step. Jaime's a little stressed out by everything so Ally tries to get her to relax by tapping on her third eye.
They go to Jaime's to get ready and wait for their friends to arrive. Jaime tells her mother she wants to loose her virginity on prom night and surprisingly her mother tells her she won't be the first. Apparently the apple doesn't fall too far from the tree. Their friends begin to arrive and the party gets started. Jaime reveals that she has a crush on Michael and thinks that someday they'll decide to be together. Michael and his date, Julia are all over each other and Jaime seems a little jealous. Who cares about Michael, Jaime, you have hottie Craig. They all pile in to the limo and head to prom. They eat and party with their friends until they just can't anymore. They go outside to get their limo to find it MIA. Apparently, Michael has let one of his friends take their limo to go uptown. The girls are not happy with Michael lending out their limo. Their limo returns and they climb in and head home. Mid-ride Craig decides he needs to get out. He drank too much "coffee" and wasn't feeling too well. He kisses Jaime goodbye and climbs out, moments later we can hear him puking. He feels extremely embarrassed that he couldn't hold his "coffee." No sex for Jaime. Jaime, Ally and Liz leave Craig behind and head home. In the morning, the girls wake up to find that poor Craig has been calling Jaime's phone. She decides that it was for the best because she really didn't want to have sex on prom night anyway.