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Will Hayes (Ryan Reynolds) is a 30-something father who is in a midst of a divorce. His 10 year old daughter Maya (Abigail Breslin) lives with her mother but is with him once or twice a week. On one of these occasions she questions him about his life before marriage. After her first sex-ed class Maya wants to know everything about how her parents met and decided to get married. In an attempt to "PG" his story, Will changes the names and some facts. In doing so, he creates a love mystery so Maya has to guess which of three women is the one he finally married. The story he tells Maya is depicted in long flashbacks. From time to time the film switches back to the present, where Maya comments and asks questions.

The story begins in 1992, where Will, a starry-eyed aspiring politician, moves away from his college sweetheart, Emily (Elizabeth Banks) to New York to work on the Clinton campaign. She gives him a closed packet and asks him to give it to her friend Summer (Rachel Weisz), a reporter. In New York, he meets April (Isla Fisher), the copy girl for the campaign. Before bringing the packet to Summer, Will opens it, it is Summer's diary. Encouraged by his roommate, he reads it, and comes across pages describing a love affair between Emily and Summer. He visits Summer to bring the diary, and meets her roommate and sometimes-lover, her college professor, a famous writer named Hampton Roth (Kevin Kline).

April and Will have a chance meeting outside work, and Will eventually practices a proposal to Emily on April. April is taken aback by Will's 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 shortly lost. Will and April eventually kiss, with Will leaving quickly and berating himself.

Emily visits and Will proposes in the park (first by recounting the story of his parents' engagement, and then by going through the words he said to April), but Emily turns him down by telling him she slept with Will's roommate. Will is heartbroken. Time goes by and Bill Clinton becomes president of the United States, and Will moves up to become speech-writer for a candidate to be Governor of New York. April travels the world, and she and Will become pen-pals. Eventually, with the encouragement of Roth, Will and Summer become romantically involved. This ends when she writes unfavorably about the politician Will works for.

Will becomes disillusioned about his choice of profession when Bill Clinton is implicated in the Monica Lewinsky scandal. He hates his job, and starts to heavily drink. In a drunken rant, he confesses romantic feelings to April, but in the process, ends up having a fight with her, telling her to "go to life rehab".

Years pass, and Will eventually finds the copy of Jane Eyre that April's father gave her. He goes to give it to her, but decides against it when he finds out that April and her boyfriend are living together.

Summer and Will bump into each other while he is at a cafe, and she invites him to a party. Emily, Will's old ex-girlfriend, also attends the party, as she now lives in New York. They end up starting up another relationship, and Emily turns out to be Maya's mother and Will's ex-wife. Will signs the divorce papers served to him.

Maya is happy that she figured out the story, but also realizes that her father still loves April, as even though Will changed the names of Emily (Sarah in real life), and Summer (Natasha in real life), he did not change April's name.

Encouraged by Maya, who wants her father to be happy, he goes to try to win April's heart. The movie ends with Will confessing he held on to the copy of Jane Eyre because it was the only thing he had of hers. Maya and Will go to April's apartment to reconcile, and the movie ends with April jumping into Will's arms to kiss him.