Cate is unprepared for the diverse reactions exhibited by Bridget and Kerry on their first day back to school since their father's death. Meanwhile, Jim tries his best to be helpful by making some questionable home improvements to the Hennessy home.

The Hennessy household and Jim are thrown for a loop when Cate's wayward nephew C.J. stops by to pay his respects to Paul and generally keep them company.

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.

Kerry gets in the art program in Europe in the summer, but Cate forgot to submit her medical records in time. Together they appeal to principal Gibb. C.J. falls for Missy's big sister Sissy and Gramps for a woman he has a car accident with.