Military contractor Brian Gilcrest (Bradley Cooper) returns to Hawaii to organize a traditional blessing for a new pedestrian gate on behalf of billionaire Carson Welch (Bill Murray), who intends to develop nearby land into a space center. Following a celebrated military career that ended in shadowy deals in Afghanistan, the now disillusioned Gilcrest is tasked with negotiating a deal with the Hawaiian natives and supporting Carson’s launch of a privately-funded satellite. Gilcrest’s mission is complicated by his former girlfriend Tracy (Rachel McAdams), now married with two children, and his idealistic Air Force liaison, Captain Allison Ng (Emma Stone), whose wide-eyed fascination with space reminds him of his own childhood sense of wonder. Gilcrest and Ng travel to meet King Kanahele at his isolated community to negotiate a deal for his participation in the gate blessing ceremony. Along the way, Ng tries to engage Gilcrest in conversation about his life and work, but is unable to break through his cynicism. When they meet the king, Ng, who is part Hawaiian, bonds with him and his companions, identifying with their spiritual view of the land and sky. After prolonged negotiations, Gilcrest brokers a deal for the king’s participation in exchange for two mountains and free cell phone service. The next night, Gilcrest and Ng have dinner at Tracy’s house, where they meet her husband Woody (John Krasinski) and their two children, Grace and Mitch. At one point, Gilcrest and Tracy find themselves alone in the kitchen, where she admits that she loved him and had plans to make a life with him before he abandoned her 13 years ago. The next evening, they attend Carson’s Christmas party, where General Dixon (Alec Baldwin) tells Gilcrest not to screw up the deal with the Hawaiians. One of the general’s men hands Gilcrest a thumb drive containing top secret information for the upcoming satellite launch. During the party, Gilcrest becomes attracted to Ng, who is having fun dancing with Carson. Afterwards, Ng joins Gilcrest in his room where he recounts his experiences in Kabul, where he almost died. He tells her that this was the first night he was truly happy to have lived, and the two make love. The next day, Ng discovers that Carson’s satellite will actually carry a nuclear payload. When she tries to resign, her colonel tells her it is a private operation run by Carson, and that Gilcrest is aware of the details. Later she confronts Gilcrest in tears for lying to her and to the Hawaiians. Meanwhile, Woody and Tracy confront each other about recent tensions in their marriage, which he believes were caused by Gilcrest’s arrival. They agree to separate. The next morning, Tracy shows up at Gilcrest’s hotel and reveals that Grace is his daughter. Later that day, after the successful blessing of the new pedestrian gate, Gilcrest learns that the Chinese are attempting to hack the satellite’s code to prevent the impending launch. He rushes to the command center and undermines the hackers’ efforts. As he watches the satellite enter geosynchronous orbit, he realizes what he’s done and its impact on Ng, whom he has come to love. Quickly he orders a massive sonic upload to be sent to space, and he and Ng hold hands as they watch the satellite explode. Believing Ng’s continued association with him will ruin her promising career, he tells her they should not see each other again. Gilcrest returns to Tracy’s house, where she reads him a moving love letter from Woody. Gilcrest tells her she belongs with her husband, and she encourages him to go after Ng. Meanwhile, Carson is not pleased with the destruction of his satellite and confronts Gilcrest, who tells him he cannot “buy the sky”. General Dixon is also incensed by Gilcrest’s actions, threatening to prosecute him. Dixon soon learns that Gilcrest was telling the truth about the weapons payload, and praises him for what he’s done and reveals that authorities will soon be taking Carson into custody. Outside the hotel, Gilcrest finds Ng, who is preparing to leave. He tells her that he loves her, that he is staying in Hawaii, and that he will be waiting for her to return. Later that night, Gilcrest stands outside Grace’s hula class and watches her dance. She notices him, he nods at her, and she suddenly realizes that he is her father. With tears of joy in her eyes, she runs outside and embraces him, then returns to her class to continue her dancing.