Against the advice of his best friend Ted, Anderson [Jason Biggs] proposes to his girlfriend Vanessa in a crowded restaurant, dressed in a Cupid costume, and the moment shatters when she suffers a fatal heart attack right there. The scene is shocking and tragic, sending Anderson into a deep, life-altering grief as he watches the person he hoped to spend forever with slip away.
Utterly devastated, Anderson quits his job and sinks into mourning, clinging to the memory of the woman he loves. A year passes, and his friend Ted notices how long Anderson has been stuck in this emotional loop, longer than the relationship itself ever lasted. To help him move forward, Ted urges Anderson to take a chance on romance again. Reluctantly, Anderson agrees, and as a test of better judgment and hope, he asks a charming waitress named Katie [Isla Fisher] to marry him — and she surprisingly says yes.
Katie, who has her own whirlwind of emotions, briefly flashes back to the night before, when she and her family — her boyfriend William [Chris Diamantopoulos], her mother Lois [Joanna Gleason], and her stepfather Stuart [Matt Malloy] — played a game of charades. William’s clue for her was “Will you marry me?” and her uncertainty prompts a visit to her imprisoned father, Smitty [Joe Pantoliano], for guidance who tells her bluntly to “Listen to your heart.” This moment of wisdom travels with her into the diner where Anderson’s proposal is taking place, shaping how she ultimately responds.
On the day Anderson and Katie begin to fall for each other, she accepts his proposal and they embark on a path that takes them from cautious optimism to a shared longing. They decide to take things slow after Katie moves into Anderson’s apartment, while Anderson obsesses over cleaning and tidying every corner as if preparing for a life together. In a rough turn of fate, Katie’s friend Matador [Ebon Moss-Bachrach] accidentally hits Anderson with a car during a walk, knocking him briefly unconscious. When he wakes, he reassures Vanessa’s memory by promising faithfulness forever, even as the real-world challenges begin to pile up.
Katie’s journey toward a future with Anderson brings them face-to-face with her family dynamics, including her mother Lois and stepfather Stuart, who become part of the growing tension as they navigate acceptance and the shadow of Vanessa’s death. Meanwhile, William remains a persistent presence, having stalked Katie and trying to win her back, complicating the budding relationship between Anderson and Katie. The tension peaks as Anderson struggles to meet Katie’s parents, and his own family pressure adds a heavy layer to every interaction.
As the wedding plans loom, Smitty makes a dramatic and emotional entrance by breaking out of jail to walk Katie down the aisle, reigniting a long-dormant spark with his ex-wife Lois and creating its own uneasy dynamic. This unexpected reunion stirs discomfort for Stuart, who finds the past resurfacing in complicated ways. When Anderson finally brings Katie to meet his own parents, his mother voices her pain and grief, blaming him for Vanessa’s death, adding another weighty layer to the couple’s fledgling bond.
Amid mounting family drama, Anderson and Katie confront the unresolved issues between them, and their feelings begin to reassert themselves with renewed seriousness. The group — including Ted and the others — rallies around the idea of a wedding, even as chaos looms. The plan to drive to Atlantic City in a car bought from Ted’s dealership becomes a reckless, all-in attempt to claim happiness in the face of unpredictable obstacles. William’s sudden assault at a rest stop, and Ted’s attempt to manage the situation — which ends with Ted crashing into a police car — lands them all under the shadow of the law.
Katie’s parents chase after the caravan, following the same destination and resorting to theft at the Tuxedo Depot in a bid to secure wedding attire and status, before they all end up in the same police station. The group’s efforts to escape lead to a daring move where Katie’s parents trick two officers and commandeer a gun, unlocking a path to freedom inside a jail cell. In a twist of fate, they all end up in a police van headed toward Atlantic City, where Anderson and Katie finally tie the knot.
The ceremony itself becomes a bittersweet culmination: married in a police van and stepping into a honeymoon that is spent in a jail, surrounded by the people who helped shape their improbable journey. What began as a heartbreak-led pursuit of a fresh start transforms into a chaotic, shared adventure that redefines what it means to find love under extraordinary circumstances.
Characters and performances weave together in a lively, offbeat narrative that blends romance, farce, and heartfelt emotion. The ensemble cast delivers a mix of warmth, humor, and small, sharp observations about love, loyalty, and the stubborn hope that a second chance can arrive when least expected. The story never shies away from its comic roots, even as it navigates grief, family ties, and the improvisational chaos that arrives when a couple’s dream of a simple wedding spirals into a citywide escapade led by a band of eccentric allies. The result is a film that feels both familiar in its emotional core and refreshingly odd in its twists, inviting audiences to root for a couple whose stubborn optimism keeps nudging them toward a shared future, against all odds.
