Definitely, Maybe 2008

As Will Hayes (Ryan Reynolds) navigates the tumultuous landscape of his divorce from Sarah (Elizabeth Banks), his 10-year-old daughter Maya (Abigail Breslin) demands to know the intricacies of their love story. Reluctantly, Will agrees to spin a yarn, but with a twist: he’ll modify names and details, leaving Maya to decipher which of the women from his past is indeed her mother. This elaborate ruse sets in motion a tale that takes us back to 1992, when Will left behind his college sweetheart “Emily Jones” (Elizabeth Banks) in Madison, Wisconsin, for a chance to work on the Clinton campaign in New York City.

In this new chapter of his life, Will encounters “April Hoffman” (Isla Fisher), a free-spirited fellow campaign staffer who refuses to be pigeonholed by party affiliations. She’s a breath of fresh air amidst the chaos, and her playful teasing only adds to Will’s frustration with his own stagnation. Arthur Robredo (Nestor Serrano), the campaign manager, is another source of Will’s discontent – his demanding nature only serves as a reminder that Will feels stuck in his coffee boy role.

Meanwhile, Will finds himself entwined in the orbit of “Summer Hartley” (Rachel Weisz), whose diary he had the misfortune of reading. It turns out she had a brief, torrid affair with Emily during their college days – a revelation that leaves Will reeling. Summer, however, is amused by Will’s curiosity and regards him with a certain… let’s say, allure.

As the story unfolds, we see Will struggling to find his footing in the campaign office. He begins by distributing toilet paper and bagels, but eventually earns a promotion to creating campaign stickers. His newfound talents also lead to a stint making phone calls to donors for high-stakes dinner parties – a role that surprisingly suits him.

In this way, Will’s life is on the cusp of change, marked by a series of encounters with fascinating women who will leave their mark on his journey.

As Will confides in April about his plan to propose to Emily, he rehearses every detail with precision. But April’s response - a tantalizing “Definitely, maybe” - leaves him bewildered and uncertain. The two friends venture to her apartment, where Will becomes fixated on the numerous copies of Jane Eyre that adorn the shelves. April reveals that each book holds a special significance, a personal inscription from her father given just before his passing. Despite years of searching secondhand bookstores, she remains devoted to collecting every edition with an inscription, driven by a deep longing for connection to her father’s memory.

As their conversation unfolds, Will and April share a tender kiss, but the moment is abruptly cut short as he departs without warning. The next day, Emily arrives in New York City, bringing with her a sudden shift in Will’s plans. However, his proposal is met with an unexpected confession: she has slept with his roommate, urging him to move on and pursue his ambitions.

The aftermath of this revelation sees Will establish a political consulting firm, staying closely tied to April as she embarks on a global journey. It is during this period that he encounters Summer, now a journalist and single, at the release party for Hampton’s new book. As they begin a romantic relationship, April returns from her travels, intent on confessing her love for Will but instead discovering his plans to propose to Summer.

Will learns that Summer has penned an article that will irreparably damage his candidate’s campaign, prompting him to plead with her not to publish it. However, she refuses, and their relationship ultimately ends in heartbreak. The article’s publication proves disastrous, derailing the campaign and costing Will his political career and friendships.

Years later, April reaches out to Will, who has slipped into depression following a series of setbacks in his new job. Meanwhile, she has moved on with her life, now in a romantic relationship with Kevin. She decides to throw Will a birthday party, reuniting him with his old colleagues. As the night wears on and Will becomes increasingly intoxicated, he confesses his love for April, only to be met with an argument about the state of their lives.

As fate would have it, Will stumbles upon a bookstore and finds the inscribed copy of Jane Eyre that has been eluding April for so long. He decides against returning the book to her apartment when he encounters Kevin, who is now living with April. Instead, Will runs into Summer, who reveals that she is expecting a child. This unexpected turn of events leads him to a party where he reunites with Emily, who has recently relocated to New York City.

In the present day, Maya’s keen intuition deduces that “Emily” is actually her mother. As Maya hopes for her parents’ reunion, the divorce is finalized, and Will assures her that she is the story’s happy ending.

As Will settles into his new living space, a chance discovery sparks a poignant epiphany. Amidst the unpacking chaos, April’s book catches his eye, prompting him to finally make amends by presenting it to her. However, his apology is met with an unexpected rebuff when April demands he leave, her tone revealing the depth of hurt she still harbors.

As Will struggles to come to terms with this response, Maya’s gentle prodding prompts a revelation: without April in his life, Will is stuck in a state of emotional limbo. He had failed to acknowledge this void by not changing April’s name in the storybook, just as he hadn’t with “Emily” or Sarah, and similarly ignored the true identity of “Summer”, whose real name was Natasha.

With Maya’s encouragement, Will decides to confront his feelings head-on and pays a visit to April’s apartment. His attempt to rationalize his actions is met with resistance, however, as April refuses to let him in. Undeterred, Will and Maya depart, but their walk is interrupted by April herself, who gives chase.

In a moment of vulnerability, Will opens up about the book’s significance – it was the only tangible connection he had left to April. Her expression softens, and she invites them inside to share the story behind the book. As they sit together, the air is charged with tension until finally, Will and April lock lips in a tender moment that speaks volumes about their complicated yet enduring bond.