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When star Diana Golden performs for a gathering of sailors, shy sailor Casey Kirby goes backstage to get her autograph for his sister.  Casey is tricked into a publicity kiss with Golden for the cameras and when his buddy, Barney Waters, reports back to their buddies on ship, the kiss instantly creates Casey's reputation as a notorious ladies' man.  When Jake, a real "Don Juan," bets Barney that Casey will not be able to kiss "The Countess," a dance hall singer who is renowned for her aloofness, Barney bets his friend Spike's antique watch, and wagers spread shipwide.  Spike threatens Barney with death unless he wins the wager, and so when they dock in San Francisco, Barney immediately takes Casey to The Countess's dance hall, Swingland, and engineers Casey into sitting with the disinterested singer.

The Countess pretends to take an interest in Casey when the manager tries to force an obnoxious patron on her, and Casey ends up walking her home.  The Countess becomes charmed by Casey despite herself, and she invites him into the hillside apartment she shares with singer Bessie Dale.  Bessie returns the same night with Barney, and both couples pursue their flirtations until Barney mentions his wager to Bessie.  Bessie interrupts Casey and The Countess just as they are about to kiss and tells The Countess about the bet.  Both Barney and Casey are thrown out of the apartment, but Casey soon realizes that he is sincerely in love with The Countess and buys an engagement ring.

Bessie, meanwhile, reveals to The Countess a plan she heard from Barney, in which Casey will propose to her in order to get a kiss.  When Casey does propose, the outraged Countess throws the ring out the window, but Casey explains his sincere intentions, and they retrieve the ring.  That night during the show at Swingland, Casey tries to propose again while The Countess dances on a conga line.  The club's bouncers think he is drunk and wrestle him to the floor, and a brawl ensues involving all the visiting sailors.  Casey is dragged off unconscious as the shore patrol arrives and is later brought to trial as the initiator of the brawl.  He refuses to defend himself until The Countess strolls into the courtroom and adopts a hard-boiled attitude, pretending that she deliberately led Casey on to get the ring, and that the bouncers threw the first punch.

Casey is acquitted and in the taxi on the way to the Navy dock, Casey and The Countess are married by a minister.  At the dock, all the sailors witness Barney win his bet as Casey and The Countess finally kiss.