When a shipping clerk is recruited by his employer to help his golf game, his boss insists he conceal his humble identity at the country club.

Gerry, Connie, and Franky are small-town girls seeking wealthy husbands in New York City. But, while Connie and Franky are reckless with their affections — one bedding a married man and the other marrying a scoundrel — Gerry is determined to remain practical. As she mothers her wounded, heartbroken friends, she stalwartly but foolishly resists the advances of the good-hearted and affluent Tony Jardine.

Jerry Marsden, the son of a wealthy man, finds himself in a series of comedic misunderstandings. To prove a point or escape a social obligation, Jerry decides to take the place of his butler, who has been sentenced to a short stay in jail. While incarcerated, Jerry finds the experience surprisingly pleasant, as he receives special treatment and even manages to flirt with the jailer's daughter, Ruth Morrisey (Alice Day). Chaos ensues when his true identity is threatened and he must navigate the complexities of high society while technically being a "prisoner."