Definitely, Maybe (2008)
A political consultant tries to explain his impending divorce and past relationships to his 11-year-old daughter.
Romantic comedy: Will Hayes, a 30-something Manhattan dad is in the midst of a divorce when his 10 year old daughter, Maya, starts to question him about his life before marriage. Maya wants to know absolutely everything about how her parents met and fell in love. Will's story begins in 1992, as a young, starry-eyed aspiring politician who moves to New York from Wisconsin in order to work on the Clinton campaign. For Maya, Will relives his past as a idealistic young man learning the ins and outs of big city politics, and recounts the history of his romantic relationships with three very different women. On the campaign, Will's best buddy is Russell McCormack. They not only have similar political aspirations, they share the same type of girl problems, too. Will hopelessly attempts a "PG" version of his story for his daughter ad changes the names so Maya has to guess who he finally married. Is her mother Will's college sweetheart, the dependable girl next-door Emily? Is she his longtime best friend and confidante, the apolitical April? Or is she the free-spirited but ambitious journalist? As Maya puts together the pieces of her dad's romantic puzzle, she begins to understand that love is not so simple or easy. And as Will tells her his tale, Maya helps him to understand that it's definitely never too late to go back...and maybe even possible to find a happy ending.
On the day she has her first sex ed class, 10-year-old Maya grills her divorcing dad Will Hayes about her conception. That night, he fills her in, changing the names of the women who were in his life then to keep her guessing which is her mom: Emily, his college girlfriend when he came to New York from Wisconsin for Clinton's '92 campaign; April, edgy, a little cynical, who misses her father; and, Summer, a writer attracted to older, established men. In demanding the story, Maya's motivation is clear: to get her dad to fall in love again with her mom. Will this parent trap work? In the telling, might Will discover his true Penelope? Definitely. Maybe.
The students at PS322 in New York City have just had their first sex education class, which doesn't sit well with many of the parents and brings up many questions by the students of their parents, including the "gross" factor of if their parents really had sex to conceive them. But for ten year old Maya Hayes, the ultimate question becomes how her parents, Will and Sarah Hayes, met and fell in love and how that love disappeared on what is now the cusp of their divorce. Maya wants to know to figure out how to make a seemingly unhappy Will, which includes being unhappy in his current job as an ad executive, be happy again, hopefully with Sarah. Upon much coercion by Maya, Will finally relents but with one caveat and two assertions: he will change the names of the women involved so that Maya will have to figure out which is her mother, the story is not as simple as Maya would probably hope, but the story does have a happy ending. Will begins his story in 1992, when he, then politically active and fantasizing of one day becoming president, moves temporarily from his college stomping grounds of Madison, Wisconsin to New York City to work on Bill Clinton's presidential bid. The three primary candidates as Maya's mother are: "Emily", Will's college sweetheart, who is afraid that Will will never return from New York and if he does that his experience there will fundamentally change him; "Summer", Emily's New York based friend, a sexually liberated woman and professionally ambitious writer; and "April", the copy girl in Clinton's New York campaign office, she who challenges Will intellectually but who herself is unmotivated to do anything with her life. As Will's professional life rises and falls, and as Emily, Summer and April enter, exit and reenter his life, Maya continually changes her opinion on who she wants to be her mother. But as Will's story hits what Maya believes to be close to its conclusion (after a series of previous possible close conclusions), Maya believes she's figured out if Emily, Summer or April is indeed her mother. But Maya also learns that Will is correct in that the story is not as simple as a "Will/Sarah" happy ending and tries to help him find that happiness she feels he deserves.
- Will Hayes (Ryan Reynolds) is a 38-year-old father who is in the midst of a divorce. His 10-year-old daughter Maya (Abigail Breslin) lives with her mother but is with him twice a week. On one of these occasions she questions him about his life before marriage. After her first sex-ed class, Maya first asks and then insists on hearing the story of how her parents met and decided to get married. Will gives in, but decides to change the names and some facts, thereby creating a love mystery, with Maya guessing which of the women will be her mom. 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 Wisconsin and 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 Hartley (Rachel Weisz), an aspiring journalist. 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 Russell (Derek Luke), 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). When Will leaves, Summer kisses him, leaving Will shocked and confused.
Will and April have a chance meeting outside work, where Will reveals he is going to propose to Emily. When Will practices a proposal to Emily on April, she 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 later lost. She has spent years buying copies of Jane Eyre from secondhand stores, hoping to find the copy her father gave her. April talks about her dreams to travel around the world, which she finds herself unable to do because of her current relationship with someone she rarely sees. When Will suggests she break up with her boyfriend to fulfill her desires, the two eventually share a kiss, with Will leaving quickly and berating himself.
Emily visits New York, and Will proposes in Central 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 and confesses she slept with Will's former roommate in Wisconsin, Charlie. Will is heartbroken. Time goes by, Bill Clinton becomes president of the United States, and Will and Russell start their own consulting firm. Their biggest client is Arthur Robredo (Nestor Serrano), their former employer on the Clinton campaign who is running to be Governor of New York. April travels the world like she wanted, and she and Will become pen-pals. Eventually, with the encouragement of Roth, Will and Summer become romantically involved. In the meantime April returns from her travels as she realized that the man she truly loves is Will. However she meets him as he's buying the engagement ring for Summer. April is heartbroken, but at the time Will doesn't notice it. Will and Summer's relationship ends when Summer writes an unfavorable story about Robredo, leading to Robredo's defeat and damaging Will's career and friendship with Russell.
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 drink heavily after finding out that April is dating a new guy. In a drunken rant, he confesses romantic feelings to her, but in the process, ends up having a fight with her, telling her to "go to life-rehab". However, it may be because of these words that April returns to school.
Some time after the fight, while walking the streets of New York, Will 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 meets her boyfriend Kevin, with whom she is living.
Summer and Will bump into each other while he is at a cafe, and Summer, who is now pregnant, invites him to a party. Maya gets upset about the possibility of Summer being her mother and Will not being her natural father. However, it is revealed that Emily also attends the party, as she now lives in New York. Eventually, she and Will start up another relationship, and Emily turns out to be Maya's mother and Will's ex-wife, as Maya correctly guesses. Will explains to Maya that the happy ending all along was Maya and they share a hug and part separate ways.
At home Will signs the divorce papers served to him and unpacks his things moved from the previous house. By accident he sees the book he wanted to give April years ago and decides to visit her at her workplace, Amnesty International. After learning that she is now single again, he gives her the book, but when she finds out that he was holding on to it rather than giving it to her immediately, she becomes angry and asks him to leave her office.
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, Maya and Will go to April's apartment. Though April refuses to open the door at first, she hears Maya demand that Will tell April the story exactly as he told it to her. April still doesn't emerge, but as they turn to go back home, she comes outside. Will confesses to April that he held on to the copy of Jane Eyre because it was the only thing he had left of her. As the three enter into April's building, April jumps into Will's arms and kisses him.