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.
Paul Hennessy has grown accustomed to his stay-at-home wife Cate taking care of their son and two daughters. His job as a sports writer kept him on the road a lot during the kids' formative years. But when Cate decides to return to work as a hospital nurse, Paul takes a job as a columnist and agrees to make the duties of raising the kids a shared experience.
Paul fondly remembers the days when his daughters would sit on his lap singing silly songs, and he was their hero for scaring away monsters from under the bed. But those days are long gone.