Portrait painter and caricaturist David Grant (Ronald Colman), newly arrived in Greenwich Village, wishes Jean Newton (Ginger Rogers) good luck on a whim as they pass on the sidewalk. When Jean delivers books, a woman makes her the gift of an expensive dress. She is quarreling with her son-in-law, who had given the dress to his wife. Believing David to be lucky, Jean asks him to partner with her on a ticket for the Irish Sweepstakes. He agrees only on condition that, if their horse wins, she accompany him on a platonic trip to see the sights before she settles down to married life in Poughkeepsie, New York. She and her fiance, Frederick "Freddie" Harper (Jack Carson), are dubious about the proposition, but he talks them into it.