In need of a tutor to boost her grades, Bridget hires Jeremy, hoping to make her chance of getting into a good college better. However, after her boyfriend gets sick, Bridget tries to persuade Jeremy to take his place. 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, which ends up just being Tylenol.
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