<P> Definitely, Maybe is a 2008 romantic comedy - drama film written and directed by Adam Brooks, and starring Ryan Reynolds, Isla Fisher, Rachel Weisz, Elizabeth Banks, Abigail Breslin, and Kevin Kline . Set in New York City during the 1990s, the film is about a political consultant who tries to help his eleven - year - old daughter understand his impending divorce by telling her the story of his past romantic relationships and how he ended up marrying her mother . The film grossed $55 million worldwide . </P> <P> 38 - year - old father Will Hayes is in the midst of a divorce . After her first sex - ed class, his 10 - year - old daughter Maya insists on hearing the story of how her parents met . Will reluctantly 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 flashbacks . From time to time the film switches back to the present, where Maya comments (often critically) and asks questions . </P> <P> The story begins in 1992 when Will, an idealistic political operative, moves away from Wisconsin and his college sweetheart, Emily, to New York City, where he works on the Clinton campaign . Over the years, Will becomes involved with three women who enter his life, including Summer Hartley, an aspiring journalist, and April 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 wholehearted 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 abruptly stops and leaves . </P> <P> 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 passionate ambitions . After Clinton is elected, Will opens a campaigning business with most of his work colleagues, which enjoys a good amount of success . </P>

Who does he end up with in definitely maybe