After first meeting at a summer camp as teenagers, Emma (Natalie Portman) and Adam (Ashton Kutcher) run into each other over the next few years but never managed to stay in regular contact. Emma is now a resident at a Los Angeles hospital and Adam is a production assistant for a musical TV show. Adam's father (Kevin Kline), a former TV star, has begun a relationship with Adam's ex-girlfriend, Vanessa (Ophelia Lovibond), which leads Adam to get drunk and call every woman in his phone seeking a hookup. The next day, he wakes to find that he text-messaged Emma and had come to the house she shares with some other residents, including her best friend Patrice (Greta Gerwig). Emma leads Adam to her bedroom to retrieve his pants, where the two of them wind up having sex.
Because of both her belief that no two people were meant to be together forever and the pressures of her job, Emma proposes they have casual sex with each other before setting some ground rules to prevent their relationship from becoming too serious. At first things go well, but then Adam starts becoming jealous of the possibility of Emma being with another doctor, Sam (Ben Lawson). Although denying he is jealous, Adam starts presenting her with gifts, which she rebuffs.
Adam becomes more distraught when his father invites him to dinner with Vanessa on sanoop’s birthday, where they announce they’re planning to have a baby together. Emma, who accompanied Adam to the dinner, berates the couple while defending Adam. Adam eventually convinces her to go out with him on a date on Valentine’s Day. Things come to a head when Emma starts becoming too uncomfortable about being on a date with Adam. Adam tells Emma he loves her, but she grows angry, telling him he should go out with another woman who 'isn't going to hurt you'. Adam drops Emma off at her hospital and drives off.
Six weeks later, a script Adam had written for his show is being filmed, and Adam gets a regular writing job on the show thanks to the help of Lucy (Lake Bell), the top assistant to the show's creator who makes it clear she's attracted to him. Emma, meanwhile, has become distraught at not being with Adam, which is compounded by her younger sister Katie's (Olivia Thirlby) wedding the next day and her widowed mother (Talia Balsam) arriving with a new boyfriend.
Emma tries calling Adam, but Adam rebuffs her on the phone. Emma realizes she wants to be with him, and drives down to his home. Adam, however, arrives home with Lucy, whom Emma takes to be Adam's new girlfriend. Emma tearfully starts driving back to the wedding. Before Adam and Lucy can have sex, Vanessa calls Adam—his father is in the hospital, having overdosed on Purple Drank. Arriving at the hospital, Vanessa confesses that she doesn't want to be with an older man and that she's scared of old people. She dumps her dog off on Adam and leaves for a party. Adam talks to his father and chastises him, but tells him he'll call the next day.
On the way out, Adam calls Emma back. Adam angrily tells Emma she needs to have the conversation she wants in person – which she does; Emma’s friend and resident Shira (Mindy Kaling) noticed Adam's father arriving and called Emma. Adam and Emma reconcile, and after a morning of eating breakfast, they go together to Emma’s sister’s wedding. Emma asks, "So, what happens now?" and Adam silently holds her hand. The film concludes with a montage of events including Adam's father and Lucy having dinner as a new couple, Patrice dating Adam's roommate Eli and meeting his same-sex parents, an arrogant resident who Emma left for Adam telling Shira he thinks they should date other people (and Shira bluntly telling him she's been seeing other people during their entire relationship), the resident deciding to experiment with Shira's gay roommate, Katie going into labor, Vanessa looking horrified as she's stuck in an elevator packed with senior citizens, and Adam and Emma being happy together as a couple.
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