Mr. Drummond is lonely so Arnold and Willis set him up with a date from a computer dating service but do not know that Mr. Drummond's friend set him up with a date as well.
Mr. Drummond scolds Arnold for secretly recording other people's conversations. Arnold disobeys him and records Kimberly's boyfriend Roger making racist comments about Willis to his sister.
When Adelaide goes away, Drummond hires a temporary housekeeper to take her place. With the new housekeeper, Arnold soon realizes that she reminds him a lot of his mom and tries to arrange it so that she and Drummond fall in love.
Everyone is planning a huge surprise party for Drummond on his 50th birthday. But the real surprise is a very tragic one: On his way home, Drummond is critically injured in an accident caused by a drunk driver.
When he sees that Arnold is heartbroken after not making his Pee Wee league football team, Drummond secretly meets with the coach and agrees to buy the team new uniforms in exchange for Arnold being given a spot on the team.
With his grades down, Drummond forbids Willis to see his new girlfriend, Charlene. However, a love-struck Willis is determined to see her, even if means doing it behind Drummond's back.