Plot: Tim Lippe has led a sheltered life in Brown Valley, Wisconsin, and thus has a simplistic view of the world, he liking the comfort of knowing everyone he comes across in his small town daily life. In his naive view, he believes his once weekly sexual encounters with Macy Vanderhei, who was his seventh grade teacher now recently divorced, is true love on both their sides. He loves his job as an insurance salesman for Brown Star Insurance, owned for twenty-five years by Bill Krogstad. Tim truly tries to do what's best for his clients. Brown Star has done well as a company largely because it has won the American Society of Mutual Insurers' (ASMI) Two-Diamond award three years in a row, it awarded only to one agency a year based on private presentations made by competing agencies to the ASMI president, Orin Helgesson, at ASMI's annual convention in Cedar Rapids, Iowa. On behalf of Brown Star, those winning presentations have been made by the agency's wunderkind, Roger Lemke, who Tim and everyone else in their office truly admires. Brown Star's winning streak is threatened when just before the upcoming ASMI convention, Roger dies under somewhat shady circumstances. His death not only means that he won't be making the presentation this year, but those shady circumstances, which if they came to ASMI's attention, would taint Brown Star's reputation as ASMI has a strong Christian morality at its core. Bill decides to send Tim to the convention as Brown Star's representative despite Tim feeling non-confident in heading to the big city to fill Roger's big shoes. At the convention, Tim is ill-prepared to deal with the people he meets, from the three conventioneers with who he ultimately hangs - Dean Ziegler, Joan Ostrowski-Fox, and Ronald Wilkes - to Bree, the young woman loitering in the convention hotel parking lot, she who he is naively unaware is a hooker. They are all outside his mentality of that comfortable Brown Valley life. As Tim spends time with this group, he will have to come to some decisions about his life, including how far he is willing to go to make it four in row for Brown Star and what his decision means in a holistic sense to him.
Alternative Plot: Insurance agent Tim Lippe (Ed Helms) is sublimely naive: He has never stayed in a hotel, has never flown in a plane, has never even left his tiny Wisconsin hometown. Chosen to represent his company at a convention in Iowa, Tim meets three veteran attendees (John C. Reilly, Anne Heche, Isiah Whitlock Jr.), who set him on course for a life-altering weekend of wild times and sweet temptation.
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