A Little Deb Will Do You
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.
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More from this season
S1 E1
Pilot
Film critic Jay Sherman falls in love with actress Valerie Fox. Jay's family and friends worry that Valerie is using him to get a good movie review. Does she truly care for him?
S1 E2
Marty's First Date
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.
S1 E3
Dial 'M' For Mother
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".
S1 E4
Miserable
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.