Wings: There Once Was a Girl from Nantucket (1990)

Genres - Comedy  |   Sub-Genres - Sitcom [TV], Workplace Comedy  |   Run Time - 30 min.  |   Countries - USA  |  
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Freewheeling Brian (Steven Weber) arranges a blind date between his uptight brother Joe (Tim Daly) and local girl Cindy (a pre-Will & Grace Megan Mullally). The problem is that Cindy has "known" (in the Biblical sense) virtually every adult male in Nantucket -- including Brian. This situation plays itself out in a riotous double date, from which both Joe and Brian emerge with battle scars aplenty!