According to Jim : The Jealous Husband (2005)

Genres - Comedy  |   Run Time - 30 min.  |   Countries - United States  |  
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Dana's new boyfriend not only takes advice on women from Jim, but also uses it, quickly making him an old boyfriend. Ryan: Mitch Rouse. Chip: Chad Brokaw. Dana: Kimberly Williams-Paisley. Cheryl: Courtney Thorne-Smith.