Plot
In 1992, Gordon Townsend tells his young daughters Amy and Kim that the impending divorce with their mother was inevitable as monogamy is not realistic, repeating it like a mantra. Twenty-three years later, Amy is a heavy-drinking, over-sexed party girl who works as a columnist for a men's magazine in New York City, and is dating gym-addict Steven. Her cold British boss, Dianna, assigns her to write an article about sports doctor Aaron Conners.
While interviewing Aaron, a text from Kim insisting they move Gordon to a cheaper assisted-living facility causes Amy to hyperventilate. He calms her down, suggesting dinner. There, he praises her writing and talks about his family. After drinks, she suggests going to his place to have sex. Although it's against her rule of never sleeping over after sex, she stays the night when asked.
The next day, Aaron calls to ask if they can see each other again. Panicking, she tells him they will talk about it at the interview, then she and her friend Nikki decide it has to end. Meanwhile, Aaron's friend, LeBron James, is excited for him as Aaron has not dated for six years. Amy watches Aaron performing surgery to Billy Joel's "Uptown Girl", his favorite song. Afterwards, she tries to break it off, but he insists they like each other and should date. Amy then receives a call that her father has fallen, so Aaron drives and tends to her father.
Aaron and Amy begin dating and fall for each other. She is worried she is going to mess up, but Kim tells her she is just doing what's normal. Gordon dies from heart failure due to hoarding his medication. At his funeral, Amy and Kim have a falling out: Amy accuses Kim of not caring about Gordon as she has always been more sympathetic towards him and has developed a similar outlook on relationships and life in general over the years. Shortly after, Aaron tells Amy that he loves her; she berates him for choosing that particular day to say it for the first time.
Aaron receives a prestigious award at a luncheon and brings Amy. While he is making his speech, her boss Dianna calls and threatens to fire her if she does not answer. Amy takes the call, leaving during Aaron's speech. Afterwards, Aaron is upset that she missed it, which starts an argument. Returning home, he thinks they should not go to bed angry, so Amy rants all night. Too tired to perform a scheduled operation on Amar'e Stoudemire that morning, Aaron tells her they need to take a break. Hurt, Amy tells him they should just break up as his article got canceled. Saying "You win," he leaves.
Out drinking with her co-workers, the intern takes Amy home; their bizarre sexual encounter is interrupted by his mom, revealing he is only 16. The next day, Dianna fires her for the incident. Aaron is moping in his apartment when LeBron calls, claiming he has been injured. He rushes over to find a group waiting to conduct an intervention, including LeBron, Matthew Broderick, Chris Evert, and Marv Albert. They tell him he has always been afraid of opening up and needs to fix things with Amy, but Aaron insists it is over.
Making amends with Kim, Amy catches up; and they, Kim and her family, comfort her with a group hug. Amy decides it is time to change, clearing out all the alcohol from her apartment. She takes her Aaron story to Vanity Fair, where it is published, and she sends Aaron the magazine with the story. After attending a game at Madison Square Garden, he is called back to the court, where the Knicks City Dancers perform with Amy front and center, to Aaron's favorite songs, including "Uptown Girl". She tells him she wants to make their relationship work. They profess their love and kiss, to applause.
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