Emma (Natalie Portman) and Adam (Ashton Kutcher) are two friends who keep bumping into each other after years apart from each other. Emma and Adam meet again through their mutual friend Patrice, when Emma is a resident in a local hospital and Adam is the assistant on a High School Musical-like TV-show, with aspirations of becoming a script writer. Adam takes down Emma’s phone number, but forgets to call her.
Six months later, Adam becomes distraught, when his eccentric father (Kevin Kline), who used to be the star of a TV show called “Great Scott” is having a relationship with his ex-girlfriend Vanessa. Determined to ‘get back on the wagon’, Adam starts calling every woman in his cell phone. The next day, he wakes up after a drunken night to find out that he text-messaged Emma and came to the home she shares with some other residents, including Patrice. Emma leads Adam to her bedroom to retrieve his pants, when the two of them wind up having sex.
Because Emma does not believe in love – she believes that ‘no two people were meant to be together forever' – Emma proposes that they have casual sex with each other, setting some ground rules for each other 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. Although denying that he is jealous, Adam starts presenting her with gifts, which she rebuffs.
Adam becomes more distraught when his father asks him to dinner with Vanessa on Adam’s birthday, where they announce that 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 that 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 and submitted through Lucy, the production assistant on the show, is being filmed and Adam is set to get a writing job on the show. Emma, meanwhile, has become distraught at not being with Adam, which is compounded by her younger sister's upcoming wedding the next day and her widowed mother 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 the production assistant can have sex, Vanessa calls Adam – his father is in the hospital, having overdosed on cough syrup. Arriving at the hospital, Vanessa confesses that she doesn’t want to be with an older man, and dumps her dog off on Adam, who talks to his father and chastises him, but tells him he’ll call tomorrow.
On the way out, Emma calls Adam again. Adam angrily tells Emma that she needs to have the conversation she wants in person – which she does; Emma’s friend and resident Shira noticed Adam's father arriving and called Emma. Adam and Emma eventually reconcile, and after a morning of eating breakfast together they go together to Emma’s sister’s wedding. Emma asks, “So, what happens now?” and Adam silently holds her hand.
In the concluding pictures, it is seen that Lucy - left stranded when Adam and Emma found each other - has taken up with Adam's father, replacing the feckless Vanessa. Eli and Patrice are shown meeting Eli's two gay dads. Vanessa is seen in an elevator with old people, being visibly disconcerted. Shira is seen with Ben telling her that she wants to see hther people. Emma is later seen as the delivery doctor to an expecting mother while her husband tries to sooth her. The last scene concludes with Adam and Emma snuggling together while falling asleep.
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