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 1 · Episode 5 ·
There Once Was a Girl from Nantucket
Brian sets Joe up on a date with a woman who's been with every man on the island.
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Episode 5 of season 1 of Wings: “There Once Was a Girl from Nantucket”. Aired 1990-05-17. Watch it online free on ZapFlix.