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'The Break-Up,' 2006

Vince VaughnJennifer Aniston
Vince Vaughn plays Gary Grobowski, who wins over Brooke Meyers (Jennifer Aniston) at a baseball game by buying a her (and her date) a hotdog. The pair go on to share friends, a bowling league, and a condo in an upscale side of Chicago. Why it failed/how they broke up: The couple's increasing... Melissa Moseley / Universal Studios
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