Season 6: Episode 108: The Diplomats ClubWith Jerry heading off to meet his supermodel girlfriend Bridgette at the airport's exclusive Diplomat's Club, Elaine decides to quit working for Mr. Pitt -- until she learns that he's changing his will to include her. Stopping at a pharmacy en route to the airport, Jerry recommends several over-the-counter medications to another customer, not realizing that it's Mr. Pitt. And when Pitt collapses after taking the drugs, Elaine is suspected of trying to kill him. Meanwhile, after making a remark that his boss interprets as a racial slur, George decides Morgan should see him with one of his black friends, even as Jerry points out that he doesn't have any.
As George seeks a black man to pose as his friend, Kramer and Earl, a passenger at the Diplomat's Club, gamble on the arrival times of airplanes. Meanwhile, Jerry's short trip for a performance prior to meeting Bridgette becomes a nightmare thanks to his worrisome booking agent, Katie. And after their humorless airline pilot sees the show, he refuses to take off for the return flight to New York with Jerry on board. Desperate to get to back to meet Bridgette, Jerry calls Elaine for help. But Pitt's lawyer overhears them discussing travel arrangements and assumes it's part of a murder conspiracy.
Down by $3,000, Kramer calls Newman to help cover his gambling losses to Earl, while Jerry and Katie get lost driving back and end up crashing their rented car into a backyard pool. Then, George invites a black exterminator to lunch, only to have Morgan shocked by his comments about the restaurant's poor sanitation. And as Mr. Pitt identifies Jerry on a TV news report as the man from the pharmacy who tried to kill him, Earl accuses Kramer of cheating after realizing he won a bet that Jerry's plane would been delayed. Finally, as Jerry's half-hour with Bridgette is interrupted by the nosy pilot and Elaine is cut out of Pitt's will, George is demoted at work.