Ben, diffident and awkward, wants to be a jazz trumpeter but wastes his time drinking in Manhattan bars and trying to pick up girls with two fellow-idlers, Dennis and Tom. He is supported by his brother Hugh (the sibling with the most African-American skin-tone characteristics), who is supposed to be a jazz singer but is unable to find much work because of his old-fashioned vocal style. Hugh's career is managed by Rupert.
Ben and Hugh live with their fair-skinned, younger sister Lelia, who wants to be a writer. Initially, she is under the wing of an older boyfriend, the intellectual David, who attempts to be helpfully critical of her writing. At a party, she abandons David for a younger man, Tony, who coaxes her back to his apartment. Tony professes his love for Lelia, and despite her apparent apprehension, he takes her virginity. Afterward she is filled with ambivalence and regret about Tony and about her first sexual encounter, but they agree to continue dating. Seeing her home, he is shocked to discover that her family is black. Sensing his racial animosity, Hugh kicks David out of the apartment; he does not want his sister dating a perceived bigot. Lelia then flirts with a gentlemanly black man, also named David. They agree to date, but when they go out dancing, David expresses resentment at her modern and independent ways.
Ben, Dennis and Tom drunkenly clown around with some strange girls in a bar. When the girls' tough male cronies enter the place, tensions flare and the two sides take their argument outside, where Ben, Dennis and Tom are badly beaten up.
Hugh and Rupert get into an argument over bookings and Rupert says he no longer wants to manage Hugh. However, Hugh convinces Rupert that they should remain partners and he swears to be more flexible.
As Lelia and David head out for another date, Tony arrives at the door looking for her. He is disappointed to see her already dating another man, and she exits past him without a word. Hugh arrives home and he and Tony get into an argument over Lelia. A beaten-up and more sanguine Ben becomes the arbiter and calms down the situation. Hugh discovers he has a good booking in Chicago and leaves. Ben is the last sibling to leave the apartment and heads down the street, losing himself in the midtown NYC crowd.
