Tim Lippe, a naive and idealistic insurance agent from a small town in Wisconsin, attempts to give his former middle school teacher, Mrs. Vanderhei, a promise ring after they have casual sex. She rejects him, citing her recent divorce. A successful agent, Tim is sent to represent his company, Brownstar Insurance, at a regional conference in Cedar Rapids, Iowa, as a replacement for his co-worker, Roger Lemke, who died in an auto-erotic asphyxiation accident. Tim idolized Roger, believing that his death was merely an unfortunate accident, and that he embodied Christian values, the key criterion used to judge the winner of the coveted “Two Diamonds” award, which Roger won three years in a row.
Tim’s boss, Bill, pressures him to win again to keep the company afloat. At the conference, Lippe meets fellow insurance agents Ronald Wilkes, Dean Ziegler, and Joan Ostrowski-Fox. He also meets Bree, a prostitute who works the parking lot in front of the hotel. She affectionately calls him “Butterscotch” after he offers her candy. Initially wary of the conference-goers, he spends more time with Ron, Dean, and Joan, and develops genuine friendships, including a crush on Joan. All the insurance agents participate in a scavenger hunt. Tim and Joan win, they bond over dinner, get intoxicated and join Dean in the hotel swimming pool. Tim and Joan begin kissing and are caught by Orin Helgesson, president of ASMI. Tim and Joan flee to her hotel room and have sex.
The next morning, Tim is guilt-ridden and calls Vanderhei to confess, before desperately asking her to marry him. After rejecting him, she suggests to Tim that he take the opportunity to start a new life. Tim returns to Joan, who attempts to comfort him by telling him what Lemke was really like: a sexual deviant who bribed Helgesson for his awards. Tim refuses to believe this and leaves Joan’s room.
He tells Dean about Lemke’s alleged bribery and Dean swears secrecy. However, Dean encourages Tim to stand up to Helgesson during his assessment. Under pressure, Tim ends up bribing Helgesson for the award, leaving him ashamed. Distraught, Tim comes across Bree and accompanies her to a party, where he gets high on methamphetamine and inadvertently starts a fight. Ron, Joan, and Dean rescue them.
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At the hotel, Bill appears at Tim’s door to inform him that with the successful acquisition of another Two Diamond award, he has sold the company which will result in the branch’s closure. Ron, Joan, and Dean begin calling Tim’s clients in an attempt to ensure their loyalty. On the final day of the conference, Bill formally announces the sale but Tim takes over the podium and reveals that his company has unethically acquired the award every year by bribing Helgesson and confesses to doing so himself. Helgesson flees the room and a furious Bill confronts Tim, his revelations having cost Bill the sale of his company. Tim responds by announcing his intention to leave the company and start another with his clients from Brownstar, 17 of which have agreed to stay with him. Bill storms off, dumbfounded.
As the four friends say their goodbyes and prepare to see each other next year, Joan and Tim are shown happy as friends, and Dean invites Ron and Tim to stay at a wealthy cousin’s cabin in Canada for the summer; both of them surprise Dean by gleefully accepting. The three of them and Joan go on to start their own company.
Experience the heartwarming journey of Tim Lippe and his friends in Cedar Rapids. Watch the full movie now for a tale of friendship, redemption, and starting anew. Don’t miss out on this captivating story that will warm your heart and inspire you to embrace change and growth. Watch Cedar Rapids now!