How to Lose a Guy in 10 Days is a 2003 romantic comedy film directed by Donald Petrie, starring Kate Hudson and Matthew McConaughey. It is based on a short comic book of the same name by Michele Alexander and Jeannie Long.
DETAILED PLOT
Andie Anderson (Kate Hudson) is a writer for the women's magazine Composure as the "How to", subject-matter expert. She is bored and wishes she could write about more serious topics. After Andie's best friend Michelle (Kathryn Hahn) experiences yet another break-up, Andie is inspired to write a new article titled "How to Lose a Guy in 10 Days"; she will begin dating a man and drive him away within 10 days.
Simultaneously, advertising executive Benjamin "Ben" Barry (Matthew McConaughey) is looking to branch out from his usual remit of beer and sports campaigns, and lead a prestigious advertising campaign for a diamond company. At a bar, Ben's boss, Phillip (Robert Klein) questions whether Ben has enough insight into the romance typically associated with diamonds, and in response Ben wagers he could make any woman fall in love with him. His manager accepts the wager and says that if he can achieve this before an event that will take place in 10 days, he will allow Ben to lead the diamond campaign. Ben's rivals, Judy Spears and Judy Green (Michael Michele and Shalom Harlow), were at the Composure magazine offices earlier in the day and know about Andie's task. Seeing Andie at the bar, they pick her as the woman to be romanced by Ben.
Ben and Andie meet and soon start their quests, neither revealing their true intentions. Andie works hard to drive Ben insane and make him break up with her in order to complete her article, but Ben continues to stick around in hopes of making her fall in love with him. Andie gets Ben knocked out in a movie theater by talking aloud while watching a film, rapidly moves her things into his apartment, acts overly possessive and clingy, ruins his boys' poker night for him and his friends, and takes him to a Celine Dion concert when he was under the assumption he was going to see a New York Knicks basketball game.
Ben stays with her despite everything, and after coming very close to breaking up they attend couples counseling, led by Andie's friend Michelle. They agree, as a solution to their problems, to visit Ben's family in Staten Island for the weekend. While vacationing together Ben and Andie begin to form a genuine bond. Andie then tries to explain to her boss Lana (Bebe Neuwirth) that she cannot continue writing and publishing this article as she has "really got to know this guy", but Lana remains insistent upon it. Around the same time, Andie and Ben go to the company ball together where Phillip meets Andie and tells Ben that he "met her, she loves you, you win".
Seeing Ben's good news, Judy and Judy set about to sabotage him. They tell his close colleagues, Tony and Thayer (Adam Goldberg and Thomas Lennon), that Andie knew about the bet all along and was playing along to help Ben win. Tony and Thayer beg Andie to keep quiet, unwittingly making her aware of the bet. Almost simultaneously, Lana, who is unaware of Ben's role in Andie's "How To" article, reveals Andie's true intentions to Ben. Upon learning of Ben's bet, Andie attempts to humiliate Ben in front of everyone at the party, and the pair argue on stage.
They go their separate ways before Ben is shown Andie's article and encouraged to read it. She explains in it how she "lost the one person she ever fell for", and, when he hears she quit her job at Composure and is on her way to Washington, D.C. for an interview, he chases her taxi and stops her. Once he accuses her of running away, they reveal their true feelings for each other and the film ends with Ben instructing the taxi driver to return Andie's belongings to her home, and then they kiss.