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NOTE: This spoiler was submitted by Spectre.

We open up in a office when Dylan (Justin Timberlake) is talking to his coworkers about the layout of his blog/website. He gets a call from his girlfriend and accidentally spills coffee on his pants. He asks one guy for his pants and offers to buy lunch for him tomorrow. Dylan lies to his GF saying he is almost there. Seeing the guy whose pants he was borrowing goes commando, he commands another coworker to give him his pants instead.

Meanwhile Jamie (Mila Kunis) is outside a movie theatre talking to her boyfriend, telling him she is outside the theatre waiting for him. It cuts back and forth between Dylan and Jamie talking on their phones. You think they are talking to each other....

They're not. They are on other sides of the country actually. Jamie meets up with her boyfriend Quincy (Andy Samberg) in New York for a showing of Pretty Woman. Jamie says she brought him his favorite sandwich and they need to hurry as the movie is about to start. Quincy says they need to talk. Quincy is breaking up with her saying they need to "chill for a bit." When Jamie says he said she was his soul mate when they had sex at that Bed and Breakfast, Quincy said that didn't count which pisses her off. Nevertheless, Jamie is not too mad at the breakup and asks why he is doing it for purely research reasons. Quincy says she was emotionally damaged, expecting someone to sweep her off her feet while not actually paying attention to the person trying to do that. Plus she had big eyes "which really freaked me out." Quincy said. Jamie is deflated from another bad relationship and pledges to stop believing in romantic comedy BS that has been shoved down her throat for years.

Meanwhile, in LA, Dylan meets with his girlfriend Kayla (Emma Stone) at a John Mayer concert. Kayla is pissed that he was late so they missed "You're body is a wonderland." Kayla then proceeds to go psycho on him, telling he doesn't pay enough attention to her. Dylan is shocked that she is breaking up with him, but happy she did it BEFORE they went in because he hates John Mayer. "He is the Sheryl Crow of our generation!" Kayla screams. Dylan leaves, happy to get away from her.

Dylan has been recruited by Jamie (who is a corporate headhunter) to be new fashion editor for GQ magazine. Dylan gets to New York where Jamie meets him at the airport. Dylan says he only came to check out the offer; he likes his website and doesn't really want the job, but the free trip was too good to pass up. Plus he is afraid to "shit on the sheets" meaning bring the quality down of the magazine. Jamie takes him to his interview and tells him he will be fine. Several hours later, Jamie is still waiting for him outside and reveals that he did get the job if he wants it but the offer is only good for a few more hours. Jamie takes him around what she calls the real New York. They stop by the Brooklyn Bridge and a ocean side bar. There they bump into Shaun White (playing himself). While Shaun is nice to Jamie, he comes across almost psychotic to Dylan, as Shaun promises to kill him after Dylan makes a corny joke.

Jamie then shows him a particular building she sneaks into to get onto the roof. It is the only place in NYC where you can see the stars plus have no cell service.  Dylan thinks it is cool but Jamie shuffles him along to Times Square. Dylan mocks it calling it tourist stuff, but suddenly people start dancing in unison. Jamie wanted to show him a flash mob; dozens of people joining together in synchronized dance as a way to connect with others in the hustle and bustle of the city. Dylan tells her that she has sold him on New York and he will take the job.

After a short time home to collect his things, Dylan returns to New York and moves into a nice apartment. Jamie had left him linens as a housewarming gift, "Just in case you shit the sheets." which makes him smile. The next day he gives a pep talk to his coworkers and says he will do his best and his door is literally always open as he takes it off the hinges. Tommy (Woody Harrelson), who works in Sports comes up and welcomes him and offers that they go out "cock hunting" that night. Dylan is taken aback, and Tommy says he thought he was gay considering the department he works in. Dylan says he's not but Tommy messes with him asking from time to time if he's sure he isn't gay (a running gag). 

That same day, Jamie comes by and sees how he was settling in. Dylan asks her out to lunch since he doesn't anyone in town yet. At lunch, Dylan gets a call from his psycho ex. He mentions he is emotionally unavailable, and Jamie tells him Quincy called her emotionally damaged. They toast over their crazy relationships.

Jamie throws a small party so Dylan can meets some new people. This starts a friendship with the two as they begin to hang out more.

One night while watching a bad romantic movie, Jamie bemoans that she misses sex. Dylan echoes the sentiment. They begin to talk about how complicated it is getting sexual satisfaction and how no one seems to want it with no strings. Dylan says it is women's fault with all their emotional manipulation, while Jamie counters that it has to do more with the egos of men in bed. "Oh yeah baby, say my name--uh I'm done." she says, mocking a bad lover. "Who have you been with?" Dylan deadpans.

Dylan says casual sex is like athletics. "It's a physical act, like playing tennis." Dylan sighs. Jamie asks if he wants more beer and Dylan checks her ass out as she does. "Let's play tennis." Dylan says.

Jamie is slightly shocked by what he is suggesting, but Dylan lays out the rules; they can be pals, have sex, and be friends no matter what happens. If one wants to end it to date someone else , they will end it and it will be no big deal. Dylan and Jamie then proceed to list off physical attributes they found attractive in each. Dylan notes he liked her eyes, which takes her by surprise. They swear on an IPAD Bible app on their arrangement then head to the bedroom.

In the bedroom, they get naked, state their various sexual hangups (for example, Dylan wears his socks during sex). They start haphazardly, Jamie saying that casual sex is so college. Dylan offers to sing some Third Eye Blind and instead sings "Closing Time" by Semisonic which he claims is actually done by Third Eye Bline (another running gag). After working out some kinks, they have amazing sex.

A montage follows over the next couple weeks where Dylan and Jamie meet up and have lots of sex, while still doing friend stuff. They seem to be enjoying themselves.

Dylan plays basketball with a bunch of guys and Tommy in the park one day. When Dylan mentions he was supposed to hang with Jamie, Tommy scoffs at their arrangement, saying it never works. Dylan says Jamie is different but Tommy says she's not. Tommy says he loves women, they are the better sex, and he wishes he could be attracted to him but he's gay. Tommy jumps over the railing into the river, freaking Dylan out. He goes to investigate and it turns out Tommy has a boat since he lives in Jersey (slightly important later).

One day, in a middle of a hook up session, Jamie's mother Lorna (Patricia Clarkson) comes in unexpectedly. She is introduced to Dylan by Jamie and they both claim they are not in a relationship. "So my daughter is your slam piece?" Lorna says irate. Dylan quickly backpedals, trying to convince her Jamie is more than that, but Lorna laughs. "I'm just messing with you, slam away." Lorna tells Jamie that she left her boring fiancee and just needs a few days to get back on her feet. Lorna heads for the kitchen, and Jamie ushers Dylan out, the mood clearly broken.

Lorna talks to her daughter about her situation with Dylan, saying she is surprised that she would agree to that as she has been more of a relationship girl. Jamie ponders that. Lorna also says she wants to go on a trip with her for the 4th of July which Jamie agrees to.

Jamie talks to Dylan and says she wants to date again. They agree to end it there and seem still good to be friends. They go into the park, where Jamie is dared to talk to a random dude. The man Parker (Bryan Greenberg), gets her number and they set up a date. Dylan mocks him as a "tree watcher."

Jamie goes on a date with Parker, who is a doctor who treats kids with cancer. They have a great date and Parker asks to see her again. Dylan begins to get jealous.

Jamie goes on another date with Parker, and reveals she has decided to have a "5 Date rule" (meaning going on a minimum of 5 dates before considering sex). Parker says she will be worth waiting for. Jamie is smitten.

The 5th date rolls around and Jamie and Parker wind up having sex on her apartment couch. In the morning, Dylan calls her and she heads outside to talk to him about her night. She buys two coffees only to see Parker leaving.  She runs up to him and he makes a lame excuse about having to do something. He then says he can't be her prince (in actuality he was basically just being patient knowing she  would eventually put out). Jamie realizes this and calls him an asshole, and they break up. 

Jamie goes back into her apartment to find her mother gone with a note saying she went back to reconcile with her fiancee. She calls Dylan and he offers to let her come with him to meet his family. They head for LA.

Dylan's family lives right on the beach in his grandfather's old home. Dylan has a sister Annie (Jenna Elfman) and a nephew Sam, who is obsessed with magic, though as Anna says, "I'll take that over him sexting his friends any day." Also living in the house is Dylan's father Mr. Harper (Richard Jenkins) who calls Jamie "Didi" the first time they meet. He shakes it off then mentions a boat he no longer owns due to his condition (he has early set on Alzheimer's which causes him to slip in and out of lucid thinking). Anna tells her brother their father is touch and go most of the time.

Anna shows Jamie some old photos of Dylan and learns a few things about him; when he was nine he had braids since he was a fan of Kris Kross and their single "Jump Jump". He is also really bad at simple math, and had a stutter when he was younger.

That night, the family go out to dinner, where Dylan's dad mistakes Dylan and Jamie as a couple. Anna says they definitely bicker like one. "You should get her jewelery, your mother always likes that. Where is she?" Anna and Dylan look at each other; their father is having another episode. Their mother divorced their dad a decade ago. When they tell him that, he becomes irate and leaves the restaurant, horrified once more that his mind is failing him.

Later, Dylan checks on Jamie and thinks she wants to have sex because he thinks she gave a signal which she said she didn't. She then mocks him on liking Kris Kross and they laugh and dance around in her room a bit. They talk some more, and Dylan admits he never brought a girl home to meet the family before and she is different. They look at each other for a long time and Jamie kisses him. "I thought you said..." Dylan says and Jamie whispers back "I know what I said..."

They begin to make out and have sex and unlike the other times it is shown to be more tender and romantic this time.

Anna gets up to get a glass of water, and sees Dylan leave Jamie's room.

In the morning, the family has breakfast and Jamie and Dylan share some banter, while Anna and Mr. Harper share a knowing look.

Dylan and Jamie go on a hike near the Hollywood sign. Jamie wants to get closer, but Dylan says they take trespassing seriously. Jamie calls him a pussy and he jumps over with her. Sitting on one of the letters, Dylan relates that he is bitter that their mother left years ago (and implied to have little to no contact with her kids or grandson). He also shows sadness at his father's deteriorating mind as he was the smartest man he has ever known.

A police chopper comes by, and Dylan screams at Jamie for being right. Jamie jumps down, but Dylan can't; he is afraid of heights, and has a phobia of helicopters as well. Jamie asks why he came up there. "Because---you--called me a pussy!" Dylan stutters. Dylan has to be airlifted away from the sign which makes his sister laugh like crazy when she sees it on the news.

Meanwhile, Jamie is playing with Sam with his saw box trick. Anna is trying to get answers from Dylan about his relationship with Jamie. Anna says he saw him come out her room. Dylan counters it is just sex. Anna tells him he has never seemed happier with her and he is in denial. Dylan says Jamie is damaged and "Magnum P.I. couldn't solve the shit in her head." Anna and Dylan run off. Jamie, who was nearby the whole time in the box, is extremely hurt by these comments.

That night at dinner, Jamie claims to have to go back to work for an emergency. She quickly says good bye and leaves. Dylan has no clue what is going on.

Dylan eventually returns back to New York and tries to call Jamie but she ignores all his calls. Jamie eventually gets a client that wants to poach Dylan from GQ but finds out later that Dylan went to the client himself.

At a photo GQ shoot, Jamie confronts him, saying by leaving GQ he is trying to screw her out of the money she would make recruiting him. They bicker some more about their supposed arrangement and Jamie leaves, bitter.

Dylan tries to call her again but it goes straight to voicemail. He gets an idea and goes to that building Jamie showed him the first night. There, she reveals he heard everything he said and tries to apologize to no avail. "Thanks for ruining my mountaintop." Jamie says apparently not wanting anything more to do with him.

Jamie spends some time with her mother, and her mother reveals though she has had many relationships, she only loved Jamie's father because she was the result. "You're my prince charming." Lorna tells her daughter and the two hug.

Mr. Harper is staying with Dylan for a few days in New York. Trying to get a table at an airport restaurant, Dylan loses his father, only to see him take an empty table and sit down with no pants on to the looks of the crowd. Seeing how everyone looks at him, Dylan joins him in solidarity, also choosing to wear no pants as they eat.

Mr. Harper has another mini episode, calling a random woman "Didi". Dylan asks who she was; his father says she was the love of his life and he fucked it all up because he was scared. He doesn't regret other things because he got to have Dylan and Anna for his children. But he never forgot Didi and he thinks it is part of the reason their mother divorced him. Dylan keys into his own situation with Jamie saying he screwed up. "If you have just a small chance, you FIX this." Mr. Harper tells his son. Dylan nods. They leave to go into the city.

In traffic, Dylan starts to call a bunch of unknown people. Mr. Harper notices they are stuck, so Dylan calls Tommy for a favor. Tommy picks them in his boat, and Dylan thanks him. Tommy says he was going their way as is and Mr. Harper is happy to be in a boat once again.

Dylan goes to get Jamie back and leaves his father in his apartment with his neighbor to make sure he doesn't have another episode by himself. Mr. Harper just nods to this and says to tell Jamie he said hi.

Jamie is at the train station to apparently meet her mother, who she is talking to on the phone. Suddenly, a flash mob begins dancing to "Jump Jump." Her mother reveals she is not actually not there but Dylan is. Dylan called the people they met during the flash mob performances for a huge favor. The flash mob segues into "Closing Time" which Dylan finally admits is by the band Semisonic. As the flash mob continues, Dylan tells Jamie he is sorry how he treated her. He gets down on one knee ("Not what you're thinking chill out" he says) and tells her he wants his best friend back "Because I'm in love with her." Dylan and Jamie kiss passionately.

They decide to on a genuine first date and pretend they don't know each other. Within fifteen minutes they get bored with that, and get to the good stuff, making out in the middle of the restaurant.

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