After Will becomes Hilary's talent coordinator, her show goes national and she is lured to New York, where Ashley hopes to model. When Philip presides over a high-profile Hollywood case, his ambition almost ruins his marriage.
While Carlton is away at a Young Republican camp, Will cooks up a flambe of a disaster on a night when an influential judge is coming to dinner, and Will can only make it through the night with the help of Geoffrey, and other plan is not to make Phil find out.
In competition with Carlton, Will sets out to prove he's the best man for the job on Hilary's TV show by escorting a famous comedian's sister out on the town.
After learning a little something about initiative, Will jumps to Hilary's aid prior to a key business meeting at the station, meanwhile an unemployed Carlton subs for Philip on career day at Ashley's school.
Will decides to book a juror dismissed from Philip's big show-biz madam sex-scandal case for Hilary's show, which results in embarrassment for Judge Banks and some annoying apologies from Will and Hilary.
Carlton is on a roll in Vegas, celebrating his birthday at the gaming tables with Will in tow but suddenly the tables turn, and the duo enter a dance contest to recoup their losses.
After being accepted at Princeton, a worried Carlton changes his life plans and retreats to a place where everybody knows his name - the bowling alley.
Geoffrey's life changes overnight when a man claiming to be his long-lost son shows up and charms everyone - except Will, who discovers the guy's not what he seems. Meanwhile, Hilary starts writing her autobiography, and an early childhood photo reveals a shocking secret.
Philip expects Ashley to decline an offer for what he considers a degrading role in an ad by a director who could also give her a recommendation to a top New York school.
On Live with Regis and Kathie Lee, Hilary subs for Gifford but doesn't see eye-to-eye with co-host Philbin. Meanwhile, Will subs for Carlton in a golf tourney and gets buddy-buddy with Philip, making Carlton jealous.
William Shatner stars as Hilary's talk-show guest, but Will must find a way to beam him from the dentist's chair to the set. Meanwhile, Hilary's show treks to New York and Ashley insists on tagging along.
