Ned (Paul Rudd) is selling produce at a local farmer's market. The daughter of one of his customers is eating a strawberry that they did not purchase, and her Dad chastises her for it. Ned calls out to her after her father leaves and gives her an entire pint of strawberries for free. Ned is then approached by a uniformed police officer, who asks him where he may buy some weed. Ned says he obviously wouldn't tell him even if he knew where to procure such an item. The cop then says he's just had a really bad week, and Ned takes pity on him--slipping him a small bag of weed with a stalk of rhubarb free of charge. The officer insists on paying, and Ned agrees to accept twenty dollars for it. After Ned takes the money, the officer says he is under arrest. Ned thinks he is kidding, but soon finds out that the officer was quite serious.
Next we go to brief scenes of three different women. Miranda (Elizabeth Banks) comes back from a boring date and calls her neighbor (Adam Scott) to ask for help with her pilot light. Even though her neighbor is starting to have sex with another girl, he is willing to run up to help her. Natalie (Zooey Deschanel) is telling sex-heavy jokes at a nearly deserted club, populated mainly by her lawyer girlfriend (Rashida Jones)'s coworkers. Liz (Emily Mortimer) shyly tries to wow her husband (Stever Coogan) by flashing him her new Brazilian wax, but he seems rather disinterested.
After eight months in prison, Ned is released on good behaviour. He returns to his farm to find out that his girlfriend, Janet, is now dating a new guy named Billy. He wants to remain working on the farm, but Janet refuses. She also will not let him take his dog (named Willie Nelson) with him. Billy drives Ned into town and after a sad goodbye with Willie Nelson, Billy is moved and tells Ned that he'll convince Janet to rent out the goat barn to him for $500 a month if he can provide her two months rent.
Ned moves in with his mother, who hosts a family dinner every week. We find out that the three girls shown earlier are Ned's sisters. The sisters are not interested in sticking around after dinner, but as Liz leaves she mentions to Ned that her door is always open. Later, Ned meets his parole officer. He believes that their relationship is like a free therapy session from the state of New York, though his parole officer does not offer much in the way of therapy. Ned struggles to come up with answers to how he will avoid staying out of trouble, other than no longer working on the farm. The parole officer says he will put that down as avoiding former criminal associates. Ned says he will think of more answers before their next meeting.
Ned shows up at Liz's house after he tires of staying with their mother. He is put into a bunk bed with Liz's son, River. River will be given $250 a week to look after River and help her husband, Dylan, with his documentary. Ned takes River to dance class, but River is clearly more interested in the karate class next door. At home, Ned shows him the movie The Pink Panther. He is shocked that River has never seen it, but he replies that his parents will not let him watch violent movies. He says that it is not violent, and then proceeds to horse around with him using karate moves. Dylan comes into the room upset that his son is up after 10 and that Ned is using the laptop for something other than typing a resume.
Ned goes to work with Dylan the next day. He is getting permission from the ballerinas to appear in Dylan's documentary about Belarussian ballerina Tatiana. Dylan is annoyed when Ned walks in front of the camera, goofs off with Tatiana, and tells the ballerina that Dylan is married. Later, Miranda and her neighbor are nervously waiting for Ned to arrive to drive her around for her interview with Lady Arabella for Vanity Fair. She wants Ned to not talk to her interviewee, but Arabella instantly takes an interest in Ned and his farming. Miranda is not allowed to ask about Arabella's infamous relationship with her ex, though her task is to somehow pry the information out of her. Instead, the interview revolves around Arabella's charity work.
Meanwhile, Natalie has been doing some nude modeling for an artist named Christian (Hugh Dancy), with whom there is an obvious mutual attraction (Ned also does a bit of modeling for him). Christian insists that the two of them come to a self-help group meeting with him. After listening to some testimonials, the group moves to a sweat tent known as the "win room". Participants are given water after sharing a personal story. Natalie is given water, and Ned is desperate to get some water as well but cannot tell a story. He is refused, but ends up passing out and being taken away in an ambulance. Natalie and Christian head home in a taxi and end up having sex.
On another night, Ned helps Dylan unload some gear but is told to stay in the vehicle while he holds a very private interview with Tatiana. Ned reads as day turns to night, and is frightened when a police car comes up behind him. He immediately declares that he is on parole. The officer says that he is parked in a 24-hour tow zone. Ned realises that he does not have the keys and runs upstairs to get them from Dylan. He discovers Dylan and Tatiana naked. Dylan says that he was only naked so that Tatiana would be more comfortable when she reveals deeply personal secrets.
Ned and Miranda attend Arabella's charity event. Miranda had hoped to get more information out of Arabella because her boss has threatened to kill her boring piece on Arabella's charity, but she quickly passes by Miranda and heads over to talk to Ned. Ned and Arabella end up alone, and Arabella opens up about her relationship. Ned asks her out, but she politely turns him down.
Ned and River act out a Cato and Clouseau attack scene, ala The Pink Panther. Ned ends up accidentally breaking River's fingers when he finds him. At River's private school interview, he does not wish to talk about the unique instrument he has learned and dance classes, but rather about his enthusiasm for a type of martial arts that his newly out of jail uncle found on Youtube. When asked about why the uncle was in jail, Dylan quickly interjects that he was protesting whale slaughter in Japan. River says he thought he was in jail for selling drugs to a cop. Liz and Dylan clearly blame Ned for River's interview performance, and kick him out of the house. Ned defends his behaviour, but Liz will not listen. She does give him a bit of money before sending him away in a taxi.
He ends up at Miranda's house. She prefers giving him the rest of the money for rent at the goat barn to having him stay with her. Ned casually mentions Dylan's nude interview with Tatiana, and Miranda comes to the obvious conclusion that Dylan is having an affair. She immediately calls Natalie. The neighbor shows up and they bond. While Miranda is on the phone, he mentions a detail of Arabella's relationship that was not public. Miranda hangs up and demands more information, which Ned reluctantly provides. He heads out to the farm but finds out that Billy has not asked Janet about his staying in the barn, and Janet will neither let him stay nor let him take Willie Nelson. He returns to Miranda's couch.
Ned attends a party at Natalie's apartment. Ned and Natalie's girlfriend, Cindy, plot to steal Willie Nelson while his ex is at a Dixie Chicks concert. He hears a Willie Nelson remix playing outside, takes it as a sign, and starts to dance. A woman comes up to dance with him, and another man comes up and dances behind him. They say that they want to have sex with him. He starts out with the girl, but gets freaked out when the guy starts to kiss him. Ned and Miranda's neighbor, Jeremy, eat lunch the next day, and after he explains the situation Jeremy says they must find him a girl, and they start to look around the restaurant. One girl reminds Jeremy of Miranda--and Ned opines that Jeremy is clearly in love with Miranda. Jeremy says he is not interested in her, and gives several reasons for it. Ned later questions Miranda about Jeremy, and she also gives reasons for why she is not interested. Miranda gets upset when Ned tells her why Jeremy is not interested in her, and confronts Jeremy about his comments. Jeremy and Miranda then turn on Ned, who continues to slightly misstate their previous words. Before storming out, Jeremy throws Miranda's article on Arabella at Ned, saying he should read it.
Earlier, Natalie found out that she is pregnant after her one night stand. While she is performing at her comedy club to an audience including Cindy and Ned, Christian walks in. She runs off to throw up in the toilet. Ned checks on her, and she tells him about her dilemma. He says that it is best to inform Cindy and that if they are truly in love they will weather the storm.
The family is gathered together with Ned, Cindy, and River on the trampoline outside and the sisters in the kitchen together. Liz talks about her marriage, and Miranda brings up what Ned told her about Dylan and Tatiana. Liz is in denial and blames Ned, but her sisters question her on why she no longer dresses in an attractive manner. Liz says that Natalie is the promiscuous one, which causes Natalie to storm out. In tears, Liz goes outside and takes River, meanwhile chastising Ned for his infantile behaviour. Liz confronts Dylan, but rather than admitting the affair he turns it back on her, attacking her mousy passive-aggressive tactics. Dylan says he would rather leave than have their children overhear him be forced to fight with her.
Miranda takes Ned into the Vanity Fair office to sign off on the validity of Arabella's story. But Ned is upset that his sister is using the information. Miranda says he never told Arabella they were off the record, but he counters that he is not a reporter and she made it clear to Arabella they were not a team. He refuses to corroborate her story even though it is of great professional cost to his sister.
Ned is now staying with Natalie. When he asks her how it went with Cindy, she implies that she has told her the truth without really confirming it. It seems clear that she did not tell her, but Ned accepts her statement at face value. The next night, Cindy and Ned drive to the farm to steal Willie Nelson. They see that Janet and Billy are still home, but after the couple goes outside they continue with their mission. As they sneak in the house, Ned mentions how glad he is that Cindy and his sister stayed together. Cindy thinks he is talking about something else until Ned mentions infidelity, and then brings up the baby. Cindy calls Natalie, and when Janet hears the noise she returns to the house. Cindy walks out, still screaming on the phone, and speeds off in the car, leaving Ned behind.
Ned is now back with his mother, and goes to check in with his parole officer. Ned thanks him for his hard work, but goes on to say that all of the stress caused him to break down and smoke a joint with a neighbor. The parole office has no choice but to report him.
The sisters and River come over for another family night, and the girls are obviously not happy with him, preoccupied, and disinterested in the family game of Charades. Ned finally has an outburst, screaming and cursing at his sisters for being so self-centered and negative. The family is shocked that the always laid-back Ned has exploded in anger. The doorbell rings and Ned answers to find his parole office and another police office there to arrest him. Miranda posts bail, but Ned decides to stay in jail. River says he knows how to get Ned to agree to sign the release form, and they make a U-turn and head out to get Willie Nelson back. Janet still refuses, saying she loves the dog. Miranda says nobody could possibly love anything as unconditionally as Ned does and that the dog truly belongs with him. Janet is unmoved, but Billy and Ned's mother come out of the house with the dog and put it into the car. Willie Nelson runs down the hallway of the jail to Ned's cell, where Ned is overjoyed to be reunited with his dog. Miranda finally realises that she belongs with Jeremy, and runs down to him in her sweats. River is seen wearing a karate outfit, with Liz encouraging him.
Some time later, Ned is eating lunch with all three sisters. Miranda and Jeremy seem to be doing well as a couple, and Liz has started to date again. Natalie gets a call from Cindy, who wants to go to the OBGYN with her. Ned decides that the city is not a fit for him and Willie, and he says it is time for him to go. Ned and Billy open up a handmade candle shop and think they should thank Janet for getting them together. Ned then wonders where Willie Nelson is, and he finally finds him with another dog in a park. The other dog's owner rounds the corner, and it is clear that the two humans have something in common. She says that her dog is named Dolly Pardon. He responds that his is Willie Nelson, and he smiles.
The credits include film outtakes throughout.
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