Ally Darling (Anna Faris), a 30-something woman struggling to make better life decisions, reads an eye-opening magazine article that warns women who've slept with 20 or more lovers have difficulty finding a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends. Along the way, she meets Colin Shea (Chris Evans), a musician and her neighbor, who helps her track down all her exes in exchange for letting him come to her place after his one-night stands.
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