Carnegie Mellon English Professor Lawrence Wetherhold (Dennis Quaid) is a middle-aged widower grappling with deep-seated depression and arrogance. Isolated from his two children and detached from his students, his life takes an unexpected turn with the arrival of his slacker brother Chuck (Thomas Haden Church), who comes seeking financial assistance and a place to stay. Meanwhile, Lawrence's teenage daughter Vanessa (Ellen Page) navigates her own struggles as she tries to connect with her uncle while feeling the weight of her father's indifference.
One fateful day, Lawrence suffers a seizure after an ill-fated attempt to retrieve his briefcase from an impounded car, leading him to the hospital. There, he meets Janet (Sarah Jessica Parker), a sympathetic doctor and former student whose past crush on him adds a complicated twist to their interactions. Following an awkward first date marred by Lawrence's arrogance, their relationship faces further strain due to Lawrence’s unresolved grief over his late wife. Despite his best efforts to reconcile during a second date, Janet starts to feel overwhelmed by his emotional neediness and ultimately decides to cut ties, leaving Lawrence in a state of confusion.
In the midst of a chaotic Christmas dinner with the Wetherhold family, Janet unexpectedly shows up bearing a cake, sparking a flurry of events that lead to further complications. After Chuck encourages Vanessa to celebrate her early acceptance to Stanford University, a drunken moment leads to unexpected tensions, and Chuck subsequently moves in with Lawrence's son James (Ashton Holmes) in his college dorm.
Amidst the chaos, James' girlfriend and Lawrence's student Missy (Camille Mana) shares the exciting news that James' poem has been accepted by The New Yorker, only to highlight Lawrence's struggles as he fails to get his academic book published. In a twist of fate, Vanessa rebrands his book into a more commercially appealing title, leading to its acceptance by Penguin Group, despite Lawrence’s reservations about the edits made by the publisher.
As Lawrence’s life continues to spiral, Janet accidentally discovers she's pregnant, a revelation that comes at a particularly tumultuous time in their relationship. With Lawrence focused on his newfound publishing success and his ambition to become the chair of the English Department, Janet grapples with her growing frustration over his self-absorption.
Ultimately, Lawrence finds himself at a crossroads, challenged by both Chuck and James to become more engaged in their lives. Encouraged by Chuck, he seeks out Janet to reconcile, learning of her pregnancy. By the end, he begins to embrace the role of a more attentive parent and a better professor, leading to a touching conclusion where the characters cradle twin babies in the end credits, symbolizing a new beginning and the themes of family and connection amidst the trials of life.
