Conrad Bloom is the ultimate nice guy. As a young advertising copywriter working in the Big Apple, Conrad is constantly putting his professional and personal dreams on hold. In the opener, Conrad thinks he may have found his one true love in Allison, but keeps breaking dates with her to (1) be a dance partner for his mom; (2) bail his activist-sister Nina out of jail; (3) baby-sit for his art director, Shelley; (4) comfort his ex-girlfriend Molly; and (5) save the job of a brain-fried co-worker.
The ad team scrambles to find a celebrity named Jerry to promote a client's potato chips after Shelley lies about landing Jerry Seinfeld. Also, Conrad tries to prove to Nina that their mother loves them equally.
Conrad finds his friendship with Molly threatened by a jealous new boyfriend. Meanwhile, he tries to persuade his sister and lonely mother to live together.
A breast pump wreaks havoc for Conrad who falls for a woman with great Yankees seats---then he sees her tattoo. Meanwhile, Florie meets an old foe.
Conrad hopes to impress his boss Faye by showing up at her party in a Titanic outfit with Molly.
Conrad gets himself in hot water when he accidentally erases a tape of the birth of Shelley's daughter. Meanwhile, an ""old"" friend from college is about to make the big leap -- and Molly's a bridesmaid.
A rock star Conrad dated in college has written a song about him. Meanwhile, Florie wants to win at tennis, in order to get back all the collectibles she's lost to Adele.
Conrad is nearly left holding the bag when his mother asks him to help her sell a line of tacky homemade purses. Meanwhile, Molly covets a shot at a big photography account with Conrad's firm.
Conrad gets a new apartment, but gets no chance to enjoy his new bachelor pad when his mother loses her house to the IRS, and she and Conrad's sister move in with him.
Conrad is surprised to discover why his mother needs a job wrapping packages; Molly has a new date.
Conrad's new girlfriend begins to irritate him with her constant analysis of their relationship.
Conrad is thrilled when his widowed mother Florie tests the romantic waters with down-to-earth Dr. Teddy Margolis, but when she suddenly breaks up with the good doctor, her disappointed son sets out to rekindle their relationship. Jane Carr also guest-stars as Teddy's receptionist, who helps fan the flames.
Florie has a great aunt who is old, mean and happens to be dying. Conrad, Nina and Florie go to the hospital to suck up to the aunt for her cash, when they realize, however, that she has no will. Furthermore, a young guy has latched onto her and claims he's in love. Meanwhile, Molly needs to get a job because her photography career is not taking off. Her new job? A Monica Lewinsky look-a-like. (NBC)
Conrad falls head over heels for his new neighbor, but stumbles even further when she asks him for a favor. Meanwhile, Nina and her boyfriend have a falling out after a dietary dispute.
Conrad dates a young female ventriloquist whose dummy is based on an old boyfriend. Eventually, she replaces her dummy with one resembling her new boyfriend, Conrad, but the new act bombs, and Conrad's shattered when he discovers that she's 'cheating' on him with her old dummy. Meanwhile, Florie strong-arms the super into doing work on their apartment, but has to become the super's servant when he threatens to blow the whistle on their illegal sublet (the apartment is zoned to house only two people, not three). (NBC)