When the actress Valerie Fox starts working at Jay's show, they fall deeply in love and start a romantic relationship. But this could be in jeopardy when Jay criticizes Valerie's performance in her latest movie.

Jay, noticing everyone in New York has a fiancee except him, begins to feel unloved. Things change when he goes to review the movie, Indecent Proposal II, and falls in love with the projectionist screening the movie. They arrange a date at her house where she is revealed to have an obsession with Jay to the point where she kidnaps him and ties him to a bed holding him hostage.

Marty invites his Jay to career day at his school where Marty develops a crush on a Cuban girl named Carmen. They go on a date but when Carmen decides to fly back to Cuba, Marty follows her and Jay must get his son back.

Jay is considered to be one of the most unpopular men on Earth (ranking even worse than Adolph Hitler) so Duke attempts to spruce up the show to get more people interested. When this doesn't work, Jay decides to soften his image by going on the "Geraldo Show" with his mother but Jay gets an even worse reputation when his mother embarrasses him to the point where he tells her to "shut up".

Eleanor is determined to have her daughter, Margo, attend the annual debutantes ball as it is a tradition in her family. When Margo is reluctantly forced into it, Jay decides to accompany her. Meanwhile, Jay competes in his time slot against children's idol Humphrey the Hippo.

Jay celebrates his 1000th episode but the episode is less than successful. Ratings get worse so Jay seeks image consultant, Adolph Hitmaker, for advice. The advice is unsuccessful and Jay is fired. Jay gets a new job on a show which teaches English for cab drivers but Jay is unhappy so he decides to win himself another Pulitzer Prize.