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.