Jamie Rellis (Mila Kunis) is an executive recruiter for a leading job agency in New York City and Dylan Harper (Justin Timberlake) works as an art director for a small internet company in Los Angeles. Jamie has the task of trying to recruit Dylan to interview for a job with GQ and begin working in New York City. Dylan comes to New York and after interviewing for the position learns from Jamie that he has been given an offer to work for GQ. At first Dylan is hesitant to accept and move from Los Angeles to New York, but in an effort to get Dylan to accept the job, Jamie spends the evening taking him around town trying to sell him on the opportunity and the city.
After a fun night together exploring the city, Dylan agrees to take the job. The next day, Jamie presents Dylan with the contract to sign so she can land her commission for recruiting him. Not knowing anyone else in the city, he and Jamie quickly develop a strong platonic friendship. One night, while hanging out at Jamie’s apartment watching a romantic comedy, they get on the topic of sex and relationships. They come to the conclusion that sex should not come with so many emotional attachments. As they both feel the need for a physical connection, they agree to have sex without emotion or commitment. After several trysts together, Jamie comes to the realization that this isn’t really what she wants and she would like to start dating again. She tells Dylan that they need to stop.
Jamie meets Parker (Bryan Greenberg), an oncologist, and they begin dating. After five dates, they consummate their relationship but the next morning Parker leaves and informs Jamie that he can't be the Prince Charming she wants. Furious, Jamie tells Parker off, assuring the end of their relationship. Trying to be sympathetic and to help Jamie get over the pain of the situation, Dylan suggests she come with him to California over the Fourth of July weekend while he visits his family. Jamie is very hesitant, but agrees after much persistence from Dylan. They fly to California where Jamie meets his sister Annie (Jenna Elfman), nephew Sammy (Nolan Gould), and father (Richard Jenkins). While in California strong emotional romantic feelings for each other begin to form and they share a passionate kiss, which leads to a night of close intimacy unlike any they had shared before. However the next day Jamie overhears a conversation between Annie and Dylan where Dylan claims he has no real feelings for Jamie. Hurt, she flies back to New York. A few days later, Dylan returns to New York trying to reconcile his friendship with Jamie and find out why she has been ignoring him. He finally finds Jamie and she informs him she overheard everything he said and has no interest in maintaining any kind of a friendship with him.
Soon after this Jamie discovers that Dylan may be leaving the GQ position for another job before the year elapses on his contract, which would affect her commission. She confronts Dylan about this which leads to another argument. Both begin to do some soul searching trying to come to terms with their feelings about their relationship. Jamie spends time with her mother (Patricia Clarkson), while Dylan discusses it with his sister over the phone. His sister informs him that their father, who suffers from the early stages of Alzheimer's disease, will be flying to Newark and he needs to be picked up at the airport. While eating at the airport with his father, his father, in a moment of Alzheimer's-induced confusion, incorrectly recognizes a passer-by as a woman from his past. Dylan asks him about this woman, and his father, upon regaining his lucidity, says that she was a woman he met in the Navy, that she was the love of his life, and regrets decisions he made in his youth to let her go. He tells Dylan not to let the same thing happen to him, and to go after the woman he loves if there is any chance of saving the relationship.
Dylan realizes how he really feels about Jamie after this talk with his father and decides to go after her. He calls Jamie’s mother to set up an excuse to get Jamie to go to Grand Central Station thinking she will be picking her mother up and arranges to have a flash mob dance to "Closing Time" set up to surprise Jamie at the station. When the moment comes he catches up with Jamie and tells her how he really feels. Surprised and happy by this turn of events, Jamie tells him to kiss her. After sharing a passionate kiss, Dylan suggests it is time they go on their first real date. They go to the Pershing Square café across the street, and although they attempt to keep the date casual and relaxed, the film ends with them in a sensual embrace and passionate kiss
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