Wings
Brothers Brian and Joe Hackett attempt to run an airline on the New England island of Nantucket while surrounded by their various wacky friends and employees.

Season 4 · Episode 9 ·
It May Have Happened One Night
After having a few drinks, Alex asks Joe to drive her home and when he arrives late the next day everyone assumes that they spent the night together.
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Episode 9 of season 4 of Wings: “It May Have Happened One Night”. Aired 1992-12-03. Watch it online free on ZapFlix.