Andie Anderson (Kate Hudson) writes how-to columns for Composure Magazine, the most successful women’s magazine in the country. After a co-worker is dumped by her latest boyfriend and succumbs to a bad case of the weepies during a staff meeting, Andie volunteers to write a column to help other women avoid the same mistakes. Her piece, “How to Lose a Guy in 10 Days,” will show readers what they should not do in a new relationship. She hopes that this piece will convince editor Lana Jong (Bebe Neuwirth) that she’s capable of taking on more important projects, including writing about political issues.

Meanwhile across town, Benjamin Barry (Matthew McConaughey), an ambitious ad executive, is sick of being stuck with beer and sports promotions. He has his eye on a big account for a large diamond merchant. To prove that he can write pitches for women, he bets his boss (Robert Klein) that he get a new woman to fall in love with him; he promises to bring her to a party in just 10 days.

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