Will Hayes, portrayed by Ryan Reynolds, is an advertising professional in bustling New York City who finds himself navigating the turbulent waters of a divorce from his estranged wife, Sarah (played by Elizabeth Banks). Their insightful 10-year-old daughter, Maya (Abigail Breslin), is curious about how her parents first met and prompts Will to share the story, but with a creative twist—he changes the names and key details, leaving Maya to guess who her mother is among the women of his past.
The tale commences in 1992, when Will, stepping away from Madison, Wisconsin, thinks back to his college romance with "Emily Jones" (also portrayed by Elizabeth Banks) while he embarks on his role in the Clinton campaign. In the vibrant campaign office, he encounters "April Hoffman" (Isla Fisher), a spirited co-worker who boasts her independence from party affiliations, playfully challenging Will's cynical perspective on politicians. Will also becomes involved with "Summer Hartley" (Rachel Weisz), who, it turns out, had a brief affair with Emily during college—a revelation that comes to light when a package containing Summer's diary finds its way to Will.
As the narrative unfolds, Will evolves from a mere coffee boy to making significant contributions within the campaign, earning him new responsibilities, and he begins to explore his feelings for April, who shares her tragic story of a lost inscribed copy of Jane Eyre, a cherished memento from her father. Their playful banter culminates in a kiss, but it ends abruptly when Emily arrives unexpectedly in New York, revealing her infidelity with Will's roommate and urging him to move on.
Following Clinton's victory, Will establishes a political consulting firm and maintains a connection with April even as he dates Summer, now a journalist. When Will learns that Summer's upcoming article could devastate his candidate's prospects, he conflicts with her, leading to the end of their romance and the collapse of his political aspirations.
Time passes, and a now-dejected Will is surprised when April, who is with someone new named Kevin, reaches out for a reunion. A birthday party reveals deep-seated emotions, with Will drunkenly admitting his love for April, resulting in a confrontation about their unfulfilling lives. A chance encounter in a bookstore yields the long-sought Jane Eyre, but Will hesitates to give it to April upon meeting her new partner.
When Summer informs him of her pregnancy, Will confronts their past, leading to an unexpected reunion with Emily. As Maya begins to piece together the puzzle of her parents’ past, she hopes for reconciliation. Yet, when the divorce is finalized, Will reassures her that their story has a happy ending.
While unpacking in his new space, Will stumbles upon April's book and gathers the courage to return it. A miscommunication leads to initial resistance from April, but when he shares how much he has missed her, it spurs her to invite him and Maya in to hear the whole story, culminating in a heartfelt kiss that signifies a rekindled connection.
