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 chick flick, rapidly moves her things into his apartment, acts overly possessive and sensitive 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.
They tell his close colleagues, Tony (Adam Goldberg) and Thayer (Thomas Lennon), that Andie knew about the bet all along and was playing along to help Ben win.
Andie Anderson (Kate Hudson) is a writer for a women's magazine called Composure as the "How to..." girl.
She is bored and wishes she could write more about important things such as politics, economics, religion, poverty; stuff she actually cares about.
When his boss questions Ben's knowledge about romance, Ben bets he could make any woman fall in love with him if he wanted to.
His boss accepts the bet and confirms that if he can make any woman fall in love with him before the upcoming company ball, in just 10 days, he will allow Ben to head the advertising for the new diamond company.
While holidaying together, Ben and Andie begin to form a genuine bond, and upon arriving home Ben even refers to Andie as his girlfriend.
Andie then tries to explain to 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.
"When he ejaculated, one of his assistants gave [the model] a towel." But Richardson keeps on working.
A fashion industry insider told Jezebel that "agencies 'know full well Richardson's predatory behaviour,' but that he 'tolerated because the industry folk are just sheep.
His commercial clients include Gucci, Prada, American Apparel and many celebrities.
He also recently took these photos of 20-year-old Miley Cyrus.
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.