A woman looks back at the past nineteen men she's had relationships with in her life and wonders if one of them might be her one true love.

Ally is a woman who has many ex-boyfriends who turned out to be losers. Now she believes that she can't find a good guy. But when she runs into one of her exes who is now a 'Prince Charming', she decides to look up all of her exes to see if any of them have changed for the better. When she has trouble locating them, she asks her neighbor Colin, who sleeps with a different women every night and sneaks out the morning after to avoid talking to them, to help her.—[email protected]

In Boston, the promiscuous Ally Darling is fired from her job in a marketing company. When her sister Daisy is arranging her wedding party, Ally reads an article in a women's magazine stating that women that have slept with more than twenty guys usually do not get married. Ally counts her affairs and realizes that she has slept with nineteen boyfriends. Ally decides that the next man that she sleeps with will be her husband. Ally decides to seek out her former boyfriends and asks her next door neighbor, the womanizer Colin Shea, to help her to find them to check whether any of them has improved his life. Ally and Colin become close friends. Meanwhile Ally meets Jake Adams, who was her sweetheart in high school and now is successfully managing his family's philanthropic entities. She believes she has found her Prince Charming.—Claudio Carvalho, Rio de Janeiro, Brazil

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.—Huggo