Cal Weaver, portrayed by Steve Carell, is a man in his forties who faces a life-altering shock when he discovers that his wife, Emily, played by Julianne Moore, has been unfaithful with a colleague named David Lindhagen. The painful breakup leads to Emily seeking a divorce, leaving Cal in turmoil as they share a son named Robbie. During a heated ride home after dinner, Cal, overwhelmed by his emotions, leaps from their moving vehicle, marking the beginning of his tumultuous journey.
Determined to separate from Emily that very night, Cal is quick to agree to any legal terms she suggests. However, unable to communicate her own mid-life crisis, Emily’s attempts to explain her feelings are met with Cal's desperate pleas for silence. After moving into a new apartment, Cal settles into a routine of nightly visits to a bar where he loudly laments his marital woes. It’s here that his life intersects with Jacob Palmer, a charming womanizer, portrayed by Ryan Gosling, who takes notice of Cal’s self-deprecating demeanor and decides to intervene.
Jacob, recognizing that Cal’s lack of confidence is driving women away, offers to mentor him in the art of seduction. He critiques Cal's drink choice, noting he guzzles a diluted cranberry vodka and criticizes his fashion sense, insisting that he is wrong in wearing a size 44. Jacob promises that once he’s done with Cal, Emily will regret her decision to cheat. From a thrilling shopping spree to a complete makeover that transforms Cal's appearance and attitude, Jacob instills a newfound sense of confidence in him as he learns to navigate the dating scene.
As Cal starts to embrace a more confident persona, he successfully seduces a woman named Kate (Marissa Tomei) at the same bar. Intriguingly, Cal initially misreads the situation, coming on too strong. A sincere moment allows him to reconnect with his vulnerabilities, eliciting empathy from Kate, leading to an unexpected night together. However, this newfound charm complicates his relationship with Emily, especially after his son Robbie inadvertently reveals Cal’s infidelity with Kate during a parent-teacher conference, pushing Emily to date David, despite her lingering feelings for Cal.
Meanwhile, Hannah, a law school graduate, has her own romantic struggles when her boyfriend fails to propose. After an emotionally charged rejection, she reunites with Jacob, finding an unexpected connection that transforms their initial attraction into a deeper bond. This burgeoning relationship seems to create a rift between Jacob and Cal, as he becomes increasingly preoccupied with his own issues.
In the midst of this personal turmoil, young Robbie is grappling with his feelings for his babysitter, Jessica, who harbors a crush on Cal. As Robbie makes bold efforts to win her heart, the unconventional nature of their age difference complicates things further. Cal is blissfully unaware of Jessica's affections, preoccupied with the events surrounding his divorce and new earnest attempts to win Emily back.
As tensions rise with the parents of Jessica, a series of events lead to misunderstandings that culminate in a physical altercation involving Cal, Jacob, David, and Jessica's father, Bernie. Ultimately, Cal’s journey leads him to a pivotal moment during Robbie’s eighth-grade graduation, where he refutes his son’s cynical view of love, spurring a heartfelt recollection of his own relationship with Emily. Embracing the chance for reconciliation, Cal inspires Robbie to pursue Jessica, leading to surprising connections and resolutions as the dust settles from a chaotic year filled with love, betrayal, and growth.
In the closing moments, in what can be seen as a nod to potential restoration, Cal and Emily share a laugh over the rollercoaster of their past year, suggesting that even amidst turmoil, the threads of love and family remain intertwined.
