Tim Lippe (Helms) was the guy people always thought would go places but then he just ... didn t. He s been living in über-sleepy Brown Valley, Wisconsin his whole life, still pre-engaged to his 7th grade teacher Macy Vanderhei (Weaver), while selling insurance to protect other people s dreams. But now, Tim s stalled life is about to get a kick-start because, for the first time in his 34 years, he s headed to a major metropolis - Cedar Rapids, Iowa - where he must try to save his company at a do-or-die insurance convention that, for him, will be entirely unconventional. From the minute he checks into his hotel with his ancient American Tourister and cummerbund money belt, it s clear Tim has no idea how the modern world really works. He is soon smitten with seductive Nebraskan insurance agent Joan Ostrowski-Fox (Heche) and awed by his experienced roommates...