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Following in the vein of (Roger Dodger and In the Company of Men), director Brent Huff presents a crash course on the relationship between sexual and corporate power plays in The 100 Mile Rule. The infamous rule states that one is well within his rights to sexually indulge himself with someone other than his wife or girlfriend, provided that he is more than 100 miles away from home. This so-called rule becomes a topic of hot debate when a couple of Detroit salesmen must attend a business trip. Jerry (David Thornton) is a vocal supporter of the rule, although most of his attempts to utilize it are met with contempt and disregard. Bobby (Jake Weber), however, is a family man who staunchly resists joining his friends in their visits to various escort services, strip joints, and porn shops. Unfortunately for everyone involved, Bobby falters and allows himself a sexual encounter with Monica (Maria Bello), a beautiful cocktail waitress. It turns out, however, that Monica demands payment for her services, and she has videotaped Bobby in bed with her. Although Jerry admits he orchestrated the entire thing due to a high-profile customer he had lost to Bobby, the two salesmen end up seeking advice from their senior manager Howard (Michael McKean), who has seen it all before.