01x12 The Big Goodbye
Stardate: 41997.7 Captain Picard is tasked with making a very important “first contact” meeting with a xenophobic alien race. After tirelessly working on his opening speech (in their own language), he decides to take some time off in the Holodeck. He decides to use the program of a Private Detective in early 20th century Earth with gangsters and all. However, when the aliens probe the Enterprise, it causes the Holodeck to malfunction, leaving those who are inside in great danger. The crew must rescue Picard and the others from the Holodeck, while at the same time trying to delay the alien race’s demand to begin their exchange without giving offense.