Andie Anderson (Kate Hudson) is a journalist, who works for a magazine called Composure as the "How to..." woman. She is bored and wishes she could write more about important things, such as politics, economics, religion, poverty, and so on. She soon finds herself writing an article called "How to Lose a Guy in 10 Days". Andie tells her boss that, to write more freely and creatively, she will date a man and do all the wrong things women tend to do in relationships, and record her experiences for the article.