Continuity mistake: In the scene where Andie and Ben are riding the motorcycle and she is wearing a white tank top, you can see the outline of her bra. When they go back to his parents' house and Ben takes off Andie's tank top in the bathroom, she doesn't have a bra on.

How to Lose a Guy in 10 Days (2003)
Plot summary
Directed by: Donald Petrie
Starring: Matthew McConaughey, Kate Hudson, Adam Goldberg, Bebe Neuwirth, Kathryn Hahn, Thomas Lennon, Michael Michele, Annie Parisse, Robert Klein, Shalom Harlow
Andie (Kate Hudson) works for a women's magazine as a "How To" writer. Ben (Matthew McConaghey) works as in advertising. Andie's next article is "How to lose a guy in 10 days" Her friends help her pick out a guy at a bar. Meanwhile in the same bar Ben's co-worker's bet that he can't make a woman fall in love with him in 10 days. His co-workers choose Andie and the games begin. She is trying to lose him and he is staying with her to win the bet. They end up really falling for each other, but then they find each other out. They are both angry and part ways.
Ben: Hanging with her for 10 days is gonna be no problem.
Tony: Right. That's only nine days longer than you've ever spent with any other chick, huh?
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Answer: No.