Plot: Thirtysomething single Bostonian Ally Darling believes she's at a crossroads in her life, after she is fired from her marketing job, it and the career itself which she eventually realizes she hated/hates. The area upon which she develops a preoccupation is her less than successful search for a husband, partly due to the imminent wedding of her younger sister Daisy, and partly due to a Marie Claire magazine article she reads about the number of sex partners one has ever had and the likelihood of marriage. Ally has had nineteen sex partners, almost twice the national average. Because the article states that hitting double the average means that the likelihood of ever finding a husband is near zero, and the fact that Daisy's fiancé Eddie is a man who Daisy broke up with once before, Ally comes to the conclusion that she doesn't want to be a statistical zero meaning that one of her exes is the man she was destined to marry. The problem she faces is that besides the one she knows she doesn't want, she has no idea where any of the other eighteen are. The one she thinks she wants is her high school sweetheart Jake Adams, who may be the most difficult to track down, and as such she tries to find the rest. Not knowing how to go about it, she enlists the help of Colin Shea, a musician who lives across the hall from her apartment as he states he comes from a family of cops, who are trained in investigation. Colin is a more extreme and open version of Ally in that he has one one-night stand after another, he not ever having the nerve to tell his sex partners after the fact that he plans never to see them again, he preferring to hide out until they leave his apartment. As such, Ally's payment to him is to allow him to hide out in her apartment any morning until his dates leave. As Colin progresses with his largely successful search for the exes with Jake indeed being the elusive one, Ally evaluates the men one by one. However, she may not come to the realization in those evaluations that she, over the course of her love life, has always tried to fit the mold of what her boyfriend at the time wanted instead of being true to herself as a person, and that the one with who she is destined to be with is the one who truly does know her and accepts her for who she is.
Alternative Plot: Ally Darling (Anna Faris) is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find 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.
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