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The Baltimore Sun

'The Break-Up,' 2006

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 petty squabbles cause their relationship to crumble, and a competition ensues to see who will be the first to walk away from their beloved condo. The relationship ultimately ends as Gary realizes that Brooke -- and their home -- were out of his league.Melissa Moseley / Universal Studios