Mrs. Pembrooke sets Charles up to show a cute girl who is interested in child care a day in the life of taking care of the kids. The same day, Douglas and Jason decide to have a war.
After a fight with Gwendolyn, Charles decides to take a night off from women because he can't understand them. Unfortunately for him, Lila is having a slumber party at the house the same night.
Douglas gets an "F" on his book report and Charles has to go to the school to talk to the teacher. He is in for a surprise when she turns out to be young, smart, and very pretty.
It's Halloween and Charles helps the kids prepare for the night. He also helps out Buddy who is lacking confidence over a date and wants Charles to 'accidentally' run into the girl and learn what she likes.
Douglas discovers love when he meets a strange friend of Lila's named Enid. He likes her the way she is and gets upset when Lila tries to give her a makeover.
In an attempt to improve their relationship, Charles and Gwendolyn decide to see other people. This arrangement works well until Gwendolyn gets a date and Charles finds himself jealous.
Charles plans to go home for Christmas are canceled so he stays at the Pembroke house where he has to deal with a jealous grandmother. Meanwhile, Lila gets asked out on her first date.
Charles finds himself in a bind when he wins two tickets for a Bruce Springsteen concert and both Buddy and Gwendolyn want to go with him. He also has to deal with doing the right thing with a dog that the boys brought home.
Mr. and Mrs. Pembroke are fighting and Charles needs to get a term paper done by the next morning while avoiding the many distractions that the house provides.
The Pembrokes' irresponsible cousin Elliot has decided to run for student body president on campus. With Gwendolyn's urging, Charles runs against him in an effort to do the responsible thing.
Grandma Irene comes to the house while Mr. and Mrs. Pembroke go out of town and she tries to convince Charles to work for her in the lucrative business of selling pizza.
The Pembroke house is snowed in while Mr. & Mrs. Pembroke are at the movies. Things go from bad to worse for Charles when the furnace goes off and he has to deal with the kids as well as a group of Lila's friends.
Charles and Buddy join forces to start a new business venture that will have them screen potential live-in house helpers to be trained by Charles himself. Not all candidates are quite up to their standards.
Charles, Buddy, and Gwendolyn head to Florida with some friends for spring break but things get complicated when they are all stuck in one room and then Charles and Buddy are arrested.
Lila is asked out on a date by a guy that her parents do not approve of and she must decide whether to go on the date and betray the trust of her parents and Charles.
Charles invites an old friend of Mrs. Pembroke's to the house for dinner but regrets what he has done when the guest turns out to be a condescending jerk.
Charles and Buddy prepare to leave town for summer jobs while Douglas tries to figure out which summer camp to attend. An appearance from the kids' grandfather surprises everybody.
