Bridget is horrified when Cate is asked to fill in as the sex ed instructor in her daughter's class. But Cate is in for a shock when she tries to answer a student's written question about being pressured to have sex -- and realizes it may be from Bridget. Meanwhile, Paul and Kerry are too embarrassed to look each other in the eye after watching a foreign film together that contains a sexually explicit scene.

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.

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.