William Hayes (Ryan Reynolds) is an ad executive in New York. The movie starts out with him receiving divorce papers from his wife. He leaves work early to pick up his daughter Maya (Abigail Breslin) only to discover a foyer full of screaming parents and children at the school. He is informed that the children had sex-ed that day. His daughter then tells him that they need to talk. They go home and she begs him to tell her the story, the real story of how he and her mother met. Later that night, he finally agrees to tell her the story of how he and her mother met.
It’s Wisconsin, 1992, and Will is dating ‘Emily’ (Elizabeth Banks), his college sweetheart. He’s leaving to go to New York to work on the Clinton campaign. Emily doesn’t want him to go. She thinks New York will change him too much. His roommate tells him that he shouldn’t leave because he intends to sleep with Emily. Will’s about to get into a car to go to the airport when Emily gives him a package to give to her college roommate, ‘Summer’ (Rachel Weisz). When he arrives in New York, he goes to the campaign office, thinking he’ll be writing speeches or something. He’s given a list of coffees to go pick up. We then see him doing a variety of odd jobs at the campaign office, including carrying a pile of toilet paper to the bathroom, which he drops, earning him the name ‘Toilet Paper Guy’. He meets ‘April’ (Isla Fischer), the copy girl. Later Will, missing Emily opens the package, discovering a diary, which he and his roommate read out loud discovering that Emily and Summer had a bit of a thing. He delivers the diary to Summer and meets her much older boyfriend Hampton Roth (Kevin Kline), an author. Summer kisses him and he leaves.
At the office, he gets his big break and manages to sell lots of tickets to a benefit they’re having. He’s buying cigarettes when April comes in and they insult each other’s brands. They decide to see whose last longer. April wins, and reveals that it’s her birthday but her boyfriend is too busy trying to be Kurt Cobain so she’s alone. They go to a party together and he reveals that he’s proposing to Emily, and practices how he’s going to do it with April (her answer is “Definitely, maybe. I’ll have to think about it.”). Later at her apartment he sees that she has a shelf on copies of Jane Eyre. She tells him that when she was younger her father gave her a copy of Jane Eyre, which he inscribed. He died three weeks later. Her mother accidentally sold and she’s been looking for it ever since. The copies on her shelf are ones with inscriptions that she liked. They kiss and he freaks and runs out. Emily comes to New York and they decide to go for a walk. He proposes to Emily and as he’s talking she’s telling him to just put the ring back in his pocket, to just stop. Finally she yells his name and tells him that she slept with his roommate. She goes back to Wisconsin. Clinton wins the election and the people who work with Will have a party. He and April talk about how they’d never work out. They become good friends and she goes traveling.
Its 1994 now. He runs into Summer later at a book reading of Hampton’s. Hampton suggests that she write a piece on the man Will is working for now, Arthur Robredo. She does so, and it gets him quite a bit of recognition at the office. The two start dating. Hampton has a heart attack and they go to the hospital to see how he’s doing. He tells Summer that her article wasn’t good enough and that she should have dug up more dirt on Robredo.
It’s some time later, and Clinton is coming to New York. There’s some problems. Someone forgot to put the union label on the menu so the waiters aren’t serving, the weather in Chicago is bad (Clinton’s flying in from there), and there’s a drunk guy wandering around. Will solves all of the problems and goes out into the lobby where he gets a phone call from a woman saying that she knows everything about Robredo. He looks up and sees that it’s April. She’s finally come back and he takes her on an errand with him. She tells him about how she was kissing this guy Paco on a beach in Greece when she realized that something was missing. Then she sees what they’re doing. He’s buying an engagement ring for Summer. April freaks out, but then congratulates him. He goes to meet Summer and she shows him her newest article on Arthur Robredo. Basically, it’s going to be bad if it gets out. Will tells her that if she hands it in, they can’t be together anymore. She gives him a look and he realizes that she already did. A few days later we see an article saying that Robredo is ‘out’. Will’s friend and old roommate tells him that he screwed up. A bit later he and April are out for dinner. She tells him about this new guy she’s seeing, Kevin.
Later on, Will’s not doing so great. April comes up to his apartment and drags him to his birthday party. His old friends from the Clinton campaign are there. They talk about the recent scandal and he says that Clinton messed up, but they say that they’d vote for him again any day. Right as they’re serving cake, they realize Will’s not there. April goes to her apartment, where he’s sitting on the steps, fairly drunk. He tells her that he’s always loved her. She tells him that it’s too late for that now, slaps him a couple times and tells him that he’d better get off her porch. We come back to the present and Maya’s getting very tired. She falls asleep and Will covers her up. It’s now the next day and they’re at the park. Back to the story; it’s 1997 and Will’s walking. He goes by a used book store and he sees a copy of Jane Eyre and goes to see about it. It’s the very one that April’s dad gave to her. He buys it and the next day he goes to her apartment to give it to her. She’s not there, but Kevin is. He leaves and takes the book with him. He goes to café and Summer walks by. She tells him that she’s pregnant and the father is out of the picture. She invites him to a little get together that weekend. He agrees.
At the party, they talk about Hampton and his death. She tells him that there’s someone she wants him to meet and takes him out to the patio. It’s Emily and they go for a walk in the park. They talk about how messed up everything got and how she just got scared of his ‘plan’. She touches his hair and Maya says, “Stop!” She tells Will that that’s how she knows who her mom is because she always does that when Maya’s upset. Will says that she’s right, Emily is her mom. Elizabeth Banks walks up to them and he says, “Hello Sara.” They go to the zoo with Maya and look at the penguins. Will tells Maya that the happy ending of the story is her and she goes home with her mom.
Will’s at his apartment looking through some boxes. He pulls out the copy of Jane Eyre and decides to give it to April. She’s working for Amnesty International now and she’s happy to see him and incredibly happy about the book. That is, until he tells her that he’s had it for years (since 1997). She tells him to leave and he does. Later, he’s sitting at his kitchen table with Maya and she tells him she wants him to just be happy. She asks why he didn’t change April’s name, but Sara became Emily and Natasha was Summer in the story. He really did love April all along. They go to her apartment and she doesn’t let them in at first. Maya tells Will that they need to tell her the story (April can hear them still). Will counts to 30 and when she still hasn’t let them in they leave. They get a few steps when April runs up behind them and asks them ‘What story?’ She and Will hug and Maya says that they’ll tell her all about it. They go up and as Will’s about to go in through the door; April runs back out and kisses him.
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