Als Diane Rodney, eine alte Freundin Tonys, wieder in der Stadt auftaucht, nimmt Jeannie aus Verärgerung eine Einladung Rogers zum Dinner an. Vor dem Date gibt Tony Roger noch Ratschläge in Sachen Frauen – ohne zu ahnen, dass es sich bei Rogers Date um Jeannie handelt. Der Abend endet damit, dass Tony Diane durch die ganze Stadt schleppt, um Jeannie und Roger zu finden. Schließlich bittet Tony Jeannie, nach Hause zu kommen. Doch Jeannie will lieber Rogers Plattensammlung hören.
Diane, an old girlfriend of Tony's, comes into town and invites him to pick up where they left off, making Jeannie jealous. Meanwhile, Tony's best friend, Roger Healey, who still doesn't know about Jeannie, "bumps" into her on the street and becomes immediately attracted to her, aggressively pursuing her for a date. Jeannie accepts, causing Tony to become worried and a little bit jealous about her very first mystery date. He decides to drag Diane all over town in search of Jeannie and her unidentified escort.
Roger conosce Jeannie, e senza sapere chi sia davvero, le chiede di uscire. Lei decide di accettare, ma solo per far ingelosire Tony.
Jeannie, para deixar Tony com ciúmes, marca um encontro com Roger, que acabou de conhecer. Tony incentiva Roger quando sabe que ele vai sair com uma bela garota, mas quando descobre quem é a garota, fica desesperado e sai correndo para procurá-los.
Jeannie sale con Roger para hacer que Tony celoso. Roger se enamora de Jeannie pensando que ella es una mujer normal.
