Ned, played by Paul Rudd, is a laid-back hippie who spends his days selling produce at a local farmer's market. One day, he witnesses a young girl enjoying a strawberry she didn't buy, and after her father chastises her, he kindly gifts her a pint of strawberries. Unfortunately, this act of kindness soon turns into trouble when a uniformed police officer approaches him, asking for some weed. Although Ned declines to share any information, he ultimately takes pity on the officer and gives him a small bag of marijuana. Just when Ned thinks he can continue his day unscathed, the officer gets serious, leading to Ned's unexpected arrest during a police sting operation—an important lesson learned too late about the ramifications of his actions.
The story unfolds to showcase the lives of three different women: Miranda (Elizabeth Banks), who returns from a dull date and seeks help from her neighbor, even interrupting his intimate moment; Natalie (Zooey Deschanel), performing risqué comedy in a nearly empty club; and Liz (Emily Mortimer), who tries to spice things up with her husband, Dylan (Steve Coogan), but finds him disinterested. After spending eight months behind bars, Ned is released and returns to his farm, only to find that his girlfriend, Janet, is now involved with a new man named Billy. Desperate to maintain some connection to his former life, he hopes to work on the farm, but Janet refuses to let him—further complicating his already chaotic situation.
Forced into living with his neurotic mother, Ilene (Shirley Knight), Ned learns that his sisters are the women he had seen previously—each carving their own path through life's ups and downs. As family dinners reveal personal tensions, the brothers and sisters struggle with their dynamics. With his parole officer pushing him toward improvement, Ned finds himself wrestling with how to stay out of trouble while dealing with his tumultuous relationships.
Ned eventually moves in with Liz and her family, where he takes on a peculiar new role babysitting River, Liz's ten-year-old son. Through a series of comedic mishaps, including a basketball scene where he accidentally breaks River's finger, and a late-night movie marathon that ruffles his parents’ feathers, Ned tries to bond with River while managing expectations around babysitting. As a backdrop to all this, romantic entanglements arise; Natalie, deeply attracted to an artist named Christian (Hugh Dancy), faces her own emotional turmoil which adds an extra layer of drama to Ned's existence.
The film reaches a crisis point when rumors of infidelity arise, prompting disputes among the sisters and forcing Ned to confront a whirlwind of familial and romantic drama. Ultimately, he finds himself caught in the crossfire of relationships, misunderstandings, and the stakes of personal life, as he struggles with both external and internal battles, even ending up back in jail due to a misunderstanding.
Through a series of hilarious yet poignant moments, Ned’s journey unfolds as he strives to claim his rightful place in his mismatched family. In a grand finale, the family gathers, and new beginnings spark as Ned decides to move past the city life in pursuit of something simpler, opening a handmade candle shop with Billy. As he heads out to find his loyal dog, Willie Nelson, he encounters yet another dog owner, and just like that, a chance meeting hints at what could become a beautiful new relationship. The story, woven with heartfelt moments and comedic escapades, culminates in a celebration of love, family, and the unexpected turns that life can take—all wrapped in a cozy atmosphere of genuine sincerity and laughter.
The end credits roll with entertaining outtakes and bloopers that bring a light-hearted finish to the heartfelt tale.
