Definitely, Maybe (2008)

Will Hayes (Ryan Reynolds) is a 38-year-old father who is in the midst of a divorce. After her first sex-ed class, his 10-year-old daug...

Will Hayes (Ryan Reynolds) is a 38-year-old father who is in the midst of a divorce. After her first sex-ed class, his 10-year-old daughter Maya (Abigail Breslin) insists on hearing the story of how her parents met. Will gives in, but decides to change the names and some of the facts relating to the various love affairs of his youth, thereby creating a love mystery; Maya is left guessing which of the women will turn out to be her mother. The story he tells Maya is depicted in long flashbacks. From time to time the film switches back to the present, where Maya comments (often disdainfully) and asks questions.

The story begins in 1992 when Will, a starry-eyed aspiring political operative, moves away from Wisconsin and his college sweetheart, Emily (Elizabeth Banks) to New York City, where he works on the Clinton campaign. Over the years, Will becomes involved with three women who enter and re-enter his life, including Summer Hartley (Rachel Weisz) an aspiring journalist, and April (Isla Fisher) the copy girl for the campaign. Will and April have a chance meeting outside work, where Will reveals he is going to propose to Emily. When Will practices his proposal to Emily on April, she is taken aback by Will's heartfelt words, and replies, "Definitely, maybe." They go back to her apartment, where April has multiple copies of Jane Eyre in her collection, explaining that her father gave her a copy with an inscription in the front shortly before he died, and the book was later lost. She has spent years looking through copies of Jane Eyre at secondhand stores hoping to find the copy her father gave her, but she buys any copy she finds that has an inscription. They kiss, but Will backs away and leaves.

Emily comes back to New York where she confesses, just after Will proposes, that she slept with his roommate. She did it on purpose to break up with Will, saying that she is "letting him go" because she does not share his rather lofty aspirations. After Clinton is elected, Will opens a campaigning business with most of his work colleagues, which enjoys a good amount of success.

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