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.