Plot: Benjamin, an ad executive, is trying to land a big account, only his boss thinks that it needs a feminine touch, so he considers giving it to a couple of female execs. Benjamin makes a wager with them that if he can get a woman to fall in love with him he gets the account. He lets the female execs choose the girl. They choose Andie, a writer for Composure magazine whom they had met earlier and learned she is doing an article called "How to Lose a Guy in 10 Days". Knowing that she's going to be impossible, they don't tell him that. Ben tries his best to woo her while she does her best to drive him away.
Alternative Plot: An advice columnist, Andie Anderson (Kate Hudson), tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. Her editor, Lana (Bebe Neuwirth), loves it, and Andie goes off to find a man she can use for the experiment. Enter executive Ben Berry (Matthew McConaughey), who is so confident in his romantic prowess that he thinks he can make any woman fall in love with him in 10 days. When Andie and Ben meet, their plans backfire.
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