In need of a tutor to boost her grades, Bridget hires Jeremy, hoping to make her chance of getting into a good college better. Meanwhile, Kyle treats Kerry to an very un-corporate Valentine's Day celebration. Rory gets pointers about the perfect gift for his new girlfriend Missy. Jim sends C.J. on an errand to get a special drug in Canada.

Bridget decides to make a move on her tutor but discovers that he may have his sights set on her debate team opponent. Meanwhile, after accidentally setting fire to C.J.'s van, Jim is not-so-thrilled when Cate forces him to share his basement room with him.

After being told that she's fickle when it comes to relationships, Bridget is afraid that she may end up hurting Jeremy's feelings when her ex-boyfriend returns to town. Meanwhile, Kerry is outraged and plans revenge when provocative dancing has been banned from the high school formal, which is being chaperoned by Cate and Jim. C.J. partners with Rory to broadcast school scandals over the internet.