This novel for young people is the third in the "It Girl" series of novels, inspired by the popular "Gossip Girl" series and featuring one of its important characters, Jenny Humphrey. In this particular novel, Jenny and several of her fellow students at Waverly Academy find themselves caught up in a convoluted web of romance, sex, rivalries, and illicit partying. As events unfold, the narrative explores themes related to the importance of self-respect, the tension between honesty and secrets, and the nature of responsibility.

The narrative begins as Jenny and her artsy boyfriend Easy, her driven friend Brett, her self-centered roommate Callie, her enemy Tinsley, and the rest of the students at the upper class Waverly Academy prepare for Trustee Weekend. Traditionally, Trustee Weekend has provided an opportunity for students to party while faculty and administration are busy courting the wallets and goodwill of donors and parents. At first, this particular Trustee Weekend promises to be no exception, as one of the boys (hard partying Heath) has ordered several kegs of beer for a big party. When the kegs arrive, Tinsley helps Heath and freshman Julian hide them, one on the roof and the rest under the bed of her mysterious, frequently absent dorm neighbor. Unknown to the boys, however, Tinsley has a party for the girls of her dorm, Dumbarton Hall. The party comes to an abrupt end, however, when the girls are caught. In punishment, the Dean confines all the girls in Dumbarton to their dorm for the weekend, and orders them to write an essay about what it means to be a responsible Waverly Owl. This brings everyone's plans for a party during Trustee Weekend to a similarly abrupt end.

The Dean's decision throws several romantic entanglements into disarray. Jenny is disappointed not to be spending time with Easy (which is just fine with Callie, Easy's resentful ex-girlfriend and Jenny's roommate), while Brett is unhappy about having to miss an opportunity to be with her boyfriend from another school, Jeremiah. Tinsley, for her part, is upset that she's going to be unable to follow through on her surging crush on Julian. When the Dumbarton girls gather to decide how they're going to approach the weekend and writing the essay, they agree to make the best of the faculty's absence (for Trustee Weekend activities) and have a party anyway. When the boys get word, they find a way to make their way into the forbidden dorm.

As the party gets underway, Jeremiah surprises Brett by showing up, Easy surprises Callie by making out with her, Julian surprises Tinsley by making it clear he's as into her as she is into him, and everyone is surprised by the unexpected arrival of a mysterious girl and the unexpected depths of Tinsley's neighbor, the bookish Kara. Once it's discovered that the mysterious girl is not in fact a teacher, the party resumes in the Dumbarton Common room, where a game of "I Never" quickly gets out of hand. Several secrets are revealed, several relationships are shaken up, and several partiers are forced to face the uncomfortable results of previous bad choices.

In the aftermath of the party, and as various couples struggle to put themselves and their relationships together, four Dumbarton girls (Jenny, Brett, Callie and Kara) make a pact to help each other gain both self-respect and the respect of others. This, and the story of how they came to the realization of the value of self-respect, makes up the essential content of the essay they present, as a group, to the Dean. The self-absorbed Tinsley, however, is much more focused on her future with Julian, a future which she seems to believe will be a lot of fun.