Conrad Bloom is a single New Yorker who works as an advertising executive. His life revolves around five women: ex-girlfriend/best friend Molly, who keeps him grounded; flighty sister Nina, who relies on Conrad for money, advice and clean laundry; recently widowed mother Florie, who has entered the workforce and the dating world after 30 years as a housewife; advertising agency owner Faye, an all-business dynamo; and co-worker Shelley, a new mother trying to "have it all." Another co-worker, one-time advertising star George Dorsey, could benefit from a dose of Conrad's youthful ambition.
A young copywriter finds his attempts to date a young woman continually interrupted by the other females in his life.
A lie by Shelley about landing Jerry Seinfeld forces the ad team to find a celebrity named Jerry to promote chips. Also, Conrad tries to prove to Nina that their mother loves them equally.
Conrad finds his friendship with Molly threatened. Meanwhile, he talks his jobless sister and lonely mother into living 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 enemy.
Conrad frets over a costume for Faye's Halloween party. Meanwhile, George falls for Conrad's mother after a case of mistaken identity.
Conrad accidentally erases a tape of the birth of Shelley's daughter; an "old" friend of Molly's is about to make the big leap.
A rock star that Conrad dated in college has written a song about him.
Conrad is nearly left holding the bag when his mother asks him to help her sell a line of homemade purses.
Conrad moves into a spacious apartment, but soon finds his bachelor pad---and his stlye---cramped by uninvited guests.
Conrad uncovers a secret about his late father when Florie starts looking for work. Meanwhile, Molly dates a funeral director.
Conrad breaks up with a psychiatrist-girlfriend because he doesn't like her way of analyzing everything, but he becomes upset when she and Florie remain friends.
Conrad is skeptical when Florie begins dating a doctor, until he realizes it's the best way to get his mother out of his apartment.
Florie's wealthy aunt is dying and has no will. But just as Conrad starts thinking rich, the aunt says that she's engaged.
Conrad falls head over heels for his new neighbor, but stumbles even further when she asks him for a favor.
Florie is pleased to learn that Conrad is writing comedy material for his girlfriend's act---until she finds that it reflects her comments.
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