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 7 · Episode 5 ·
Hooker, Line and Sinker
To lift Antonio's spirits after he's dumped by the "Big Faced Girl," Joe and Brian set him up with a girl at the Club Car only to discover later that she's a very expensive hooker.
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Episode 5 of season 7 of Wings: “Hooker, Line and Sinker”. Aired 1995-11-07. Watch it online free on ZapFlix.