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.
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