Paul becomes quick friends with his new editor Nick when he discovers they both are married fathers of teenage girls. But Paul soon learns that they both have the reputation of being an overprotective psycho dad. Meanwhile, Paul wants to make Thanksgiving a family affair, and forbids Bridget and Kerry from inviting their boyfriends.

After Kerry and her boyfriend break up, Paul tries to cheer her up by getting Bridget to take her little sister with her to a party. Meanwhile, Paul and Cate try to discover what is hidden in Rory's secret box.

Bridget and Paul are surprised to find themselves in similar situations when they are both alienated in their social circles. But they devise a plan to settle the score, leading Paul to crash a poker game with Tommy to get closer to boss Nick, and Bridget trying to break up ex-boyfriend Kyle and her nemesis Jenna.

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 receives a phone call that Paul had collapsed and died in the grocery store. Later that evening, Cate's parents arrive to help them through their grief.

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.

After Kerry is promoted to assistant manager at a fast food restaurant in the mall, Jim is hired to handle the register. Meanwhile C.J., who has been employed as a mall cop, busts Bridget for sneaking into a movie without paying, and Cate catches Rory selling worthless family items on the internet under false pretenses.

Cate banishes C.J. and grounds Bridget for going to C.J.'s college keg party. Jim has to take a written drivers exam after being pulled over with an expired license.

Knowing that Kerry is dragging her feet over breaking up with Kyle, Bridget takes it upon herself to do it for her sister. Meanwhile, Cate is offered the position of school nurse and Rory's first day of high school proves embarrassing when he has to hit the showers after gym class.