movie about a Nice/Shy/Nerd Girl who dates the Bully Guy

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Is there any movie about a Nice/Shy/Nerd Girl who chooses to Date the Bully from her Nice/Shy/Nerd Guy Friend? any movie where the Nice Guy lost in Date the Nice/Shy Girl but i especially look for movies where the Shy Girl chooses to date the Guy who Bully the Shy Guy



You're looking for a movie and not a TV series, but there is an episode of The Simpsons like this called "Lisa's Date With Density."



I've got two suggestions but both are different enough that they may not count. First is Just Friends but it's been awhile since I watched so I don't know if Amy Smart's character dated the bully of Ryan Reynold's character. And the second is Mr. Woodcock. But the bully in this case is marrying Sean William Scott's mom and he's his old gym teacher.