Brian Gilcrest (Bradley Cooper) discusses longing and looking up to the future as a boy. We see him in military uniform, but he then mentions that the billionaires took over in 2008 after the last financial crisis in the USA, and so he left the military and took a job as a contractor, working for a billionaire, Carson Welch (Bill Murray). He had seriously messed up in Kabul, but he now gets to go back to Hawaii, which he sees as a second chance.
As he flies over there, his pilot is John 'Woody' Woodside (John Krasinski). We are also introduced to Colonel 'Fingers' Lacy (Danny McBride), and Captain Allison Ng (Emma Stone).
Upon meeting up with Brian, Colonel Lacy jokes with him about Kabul, and tells Brian he is a big deal in Hawaii. He also informs him that his ex-girlfriend, Tracy, who is now married to Woody, handles ceremonies for the dead.
Allison Ng is Brian's Air Force liaison, very decorated and no nonsense. Tracy (Rachel McAdams) suddenly runs up to Brian though. She is surprised to see Brian there, and that Woody actually spoke to him.
Brian meets Tracy's children, her 13-year-old daughter, Gracie (Danielle Rose Russell), and her younger son, Mitch (Jaeden Lieberher), who seems to be very interested in his video camera and talking about this Hawaiian god and the arrival. Gracie seems more interested in seeing her dad. Tracy invites Brian to dinner, and Mitch hopes he will accept. Mitch asks Brian if he is the arrival.
Brian walks in on Carson talking with a biographer. Carson says he didn't abandon Brian, but rather saved him. He wants him to start with the blessing and move on from there.
While flying, Ng tells Brian tells him about a meeting with the king of the Hawaiian nation. He tells her she doesn't need to call him sir, but she still does. She also reveals that she is 1/4 (one-quarter) Hawaiian.
Once they get to the hotel, she wants to get peppermint tea, and discuss a wide range of topics, though he says there is no time for small talk or long conversations in general, and somewhat coldly tells her goodnight.
From his room, Brian can hear Ng talking about him over the phone, to her mom. She gossips about him, but also claims to see greatness, but she says she also believes him to be a wreck.
While Brian is ordering his coffee the next morning, he changes his order from a double espresso to a triple espresso since he has to be around Ng. Although he hasn't even said anything, Ng claims to appreciate his presence. As she peppers him with questions, he rolls down the window and howls like a coyote, in reference to one of the ways in which Ng had described him the night before. She finds out he had heard her then. Brian assures her he is just there as a private citizen doing work.
Gracie asks her mother why her father is in places where the war is supposed to be done with, while Tracy tells Mitch to stop playing with the camera. Gracie tells her that she seems different, and that her bad mood isn't as convincing.
Brian and Ng come to a padlocked gate to a sort of trail. Ng thinks that they're stuck, but Brian knows a shortcut, which involves hills. They joke over which one of them needs help.
Ng says that she liked to dance but broke a bone and so joined the Air Force. Brian likes to dance, but alone. Ng calls him cynical and gets him all angry. He explains that his ex-wife left him for someone interested/involved with comic books. Brian tells her that he sees what she is doing, but his brain is unpickable.
Brian and Ng come across an upside down flag, which means a nation in distress, Ng explains. They are at the nation of Hawaii. The king comes out and seems to know and be comfortable with Brian, as the two joke around.
The three of them are sitting in the king's office. Ng is honored to be there, but Brian wants to get down to business and says he just needs a 20 minute blessing and approval for a new Air Force pedestrian gate. The king tells Brian his people are crooks. Brian says that it is his nation, but they are in America, with the king seeing it as military occupation.
The three, and a bunch of others, are eating outside at night. They discuss the sacredness of the sky, and Ng absolutely affirms that weapons should not be allowed in the sky. Brian is authorized to make offerings to the king in order for the ceremony. The king wants 2 mountains back and free cell phone service. Brian says he can't really give that. Ng tells the king that she believes in Hawaii, and gives her word that the military will not put weapons in the sacred skies. She then asks him for the band to play music, and even plays the guitar with them. Brian and the king then actually agree on the deal, and the king gives him a flag.
Ng says the sky is speaking to them, but Brian says it's metaphorical and that nothing is sacred and it's all for sale. Ng tries to argue in favor of the sky, but Brian just wants to keep it about their deal with the king. She goes quiet then. Bradley Cooper does tell her about a telescope he asked his dad for in 1983. Ng asks where that guy has been.
Suddenly, there are shadows of people walking in the street. Ng tells him to stop the car and to look down. These people are supposedly ancient peoples looking for the souls of their ancestors. Ng warns him not to lift his head up, or he will be cursed.
Mitch says that he misses his dad, but Tracy tells him then he will be home tomorrow, and that also Brian is coming over then. His mother gets him food from a food truck, and Mitch sees a truck with a strange oversized load, which he films.
That next night, Ng is also over, chattering away and helping out as she tells Tracy about how she is 1/4 Hawaiian. Brian arrives, just sort of randomly popping in. Brian surprises Tracy with his presence and asks for a soda. He's brought her a poinsettia. He apologizes for Ng, but Tracy likes her. Brian and Tracy make awkward comments as to if each of them has what they want.
While Ng teaches the kids how to salute in the other room, Woody is there, but he is still silent. Brian comes in and sees a picture of Tracy in a picture frame. Brian takes out the picture and sees that it was really a picture of her and Brian.
In the kitchen Tracy tells Brian that Woody doesn't speak, but that he is a great dad. She then tells Brian she isn't ready to talk to him like a girlfriend yet. She tells him how she likes and doesn't want to lose their house, but that she is stressed out all the time with Woody being away. She tells Brian not to have any regrets and then admits she's talking to him like a girlfriend. They rehash their break-up, which involved Brian never showing up for their vacation. He saw Tracy as making it an ultimatum, which he did not like. She tells him he is a workaholic, and he says he is still working on that. She says that she loved him, and had plans, but he wrecked everything. She has waited and wanted to tell him something, which he needs to hear, about how he cannot just let people go. Woody suddenly comes in though. He comes up to touch Brian's shoulder, smiles, and leaves. Brian says he doesn't see what Tracy means, as Woody said a lot with his gestures.
Gracie comes over to them in the kitchen and says she's picked out a dress for the winter formal. As she leaves, Brian remarks that her daughter looks just like her. Brian then goes to Mitch's room and admires his collection of space items. He admits that he did almost marry his mom when Mitch asks, but won't answer why anyone would break up with her.
Instead, Brian notices a book on the arrival Mitch has. Mitch again asks if Brian is that god and tells him about the myth. Brian then tells Mitch to call him by his first name, and Mitch thinks that Brian really is that god.
Ng and Gracie are doing the hula. Woody sees them and mouths "beautiful." Brian tells Mitch he is that god, and Mitch says that he loves him.
Outside, on the Woodside's lawn, there are so many Christmas decorations it's almost tacky. Woody repeats that he loves his lawn.
Brian, Ng, Tracy and Woody all go to a holiday event. General Dixon (Alec Baldwin), a very important but irritable man, is also there. Ng goes to help Brian get the drinks.
Carson is there, talking to his biographer from before about the future. Woody looks at his wife. Brian asks Ng why she is alone on the holidays, but she says she would rather be alone. He tries to help her say in a more sexy tone that she is a fighter pilot.
General Dixon comes over to Brian and tells him not to screw up the deal with the Hawaiians. He also admits that he dislikes him and calls him a bottom feeder before walking away. Another man, Bob Largent, talks with Brian and claims that General Dixon does like him, and then slips something into his pocket. He takes his drinks and sends him to wait for Carson in the hallway.
Carson explains that they're doing what the country was meant to do, and are taking control. He was mad about Kabul, about how Brian destroyed himself by pocketing money from the Afghans. Carson tells Brian that he actually always knew of this, despite Brian thinking he never knew. He is giving him another chance though.
Carson and Ng meet and go to dance, while Brian looks on amused, as does Colonel Lacy, who is the DJ. Everyone seems to really be enjoying themselves but Brian leaves.
Back at the hotel, Brian inserts a flash drive, and sees that it contains top secret info. He sneezes and with how close their rooms are, Ng can hear him and they talk outside. She says she had fun. Brian says he's found nothing beats fun, but she says maybe purpose does. She comes over with her peppermint tea and laptop.
Ng asks about the stickers on his laptop, which he says are for each adventure. Ng then says she's never been shot and asks him what it's like. They seem to be having a moment, but then he remarks about how he messed up in Kabul.
In Kabul, Brian says he saw a missile coming but he didn't get out of the way because he didn't care. He then says that tonight was the first night he was truly happy he lived. They then kiss and are shown naked in bed together, in the middle of the night. Ng says she thinks she left her sunglasses somewhere, but they are also talking about something else, which turns out to be Brian's foot they are looking at. Brian explains that a doctor sewed another toe onto his foot.
Brian and Ng spend a romantic day together, not in their uniforms, and with Ng even in a dress.
While on a morning run, Ng seems to be in an even more excited and energetic mood than usual. She comes over to the Woodside's house, where Gracie is babysitting Mitch. Ng notices that Mitch is looking at footage he shot, which is the oversized load. They wonder what it is and guess it's a big covert operation. Ng seems distraught.
Ng wants to tender her resignation to Colonel Lacy, who is amusingly at some kind of stroller exercise morning thing. Ng wants to know what is going on, but Colonel Lacy claims he was only told what they wanted to tell him, since it's a private operation. She thinks they could be filling the sky with weapons. Once she finds out it's Carson Welch behind the program, she asks what Brian knows, but Colonel Lacy says it's more like what doesn't Brian know?
Brian buys Ng a hat before waiting to meet her for lunch at a little restaurant, complete with peppermint tea. He explains that the odd hat, which has sunglasses on it, is because of her having lost her sunglasses. He puts the hat on her, which covers her eyes, and understands her reluctance, as people have detached themselves from him before. He really wants to be a couple though. She is crying underneath the hat, which he thinks is maybe her way of saying yes to them. Ng then tells him that she knows he knows and knows what he knows, and for him to stop playing games. She got personal with him, had fun with him, believed him, and he had told her not to, which is what she is most upset about. When he says he needs her to believe in him, she just again says that she knows what he knows, and that he lied to everyone. He seemed to know about the rocket which was the oversized load, and that he was just distracting the Hawaiians. She is upset that he had her lie to the Hawaiians, especially when she is Hawaiian. Ng also tells Brian that he is lost. She then admits that she was there as his babysitter and watchdog, and everyone said he was morally bankrupt. She keeps the hat and thanks him for it as she gets in her car. She does ask if there are weapons in it though. Ng tells Brian that she was his last chance. He's sold his soul so many times that nobody is buying anymore.
Woody comes home to see his family writing thank you cards. He says very little about work when Tracy asks, even though she is clearly hoping for more from him. Tracy follows Woody to their bedroom, where he blames Brian for their problems. She says that they had problems long before he showed up though, and she can't take the silence anymore. She offers to let him stay and says that she'll leave, but he says he'll go, since he's always going anyway.
Outside, Woody destroys the Santa in the noisy Christmas display he was once so proud of.
The next morning, Tracy shows up to Brian's hotel and says she has stuff to discuss with him before he leaves. She thinks he came there for a reason. By way of asking if he has anything to celebrate on Father's Day, he confirms that Gracie is his daughter. Tracy is relieved she told him. They look down on Gracie and Mitch playing below, and Tracy tells Brian Gracie has a lot of him in her. Woody doesn't know, as it's never been discussed, with how silent he is. Tracy then admits that Woody left the night before. They briefly hold hands before she leaves.
The Hawaiians come together for a blessing of the new Air Force pedestrian gate, which will enable Carson to privatize space exploration. Everyone just looks awkward.
Bob Largent suddenly comes to take Brian and Ng with him, since the rocket launch may have been compromised by a Chinese hacker. Ng does not want to be part of it, but is obviously stuck in the car with them.
The three have to move quickly to ensure the launch, which is ahead of schedule, goes well. Colonel Lacy is also there. Brian gets his laptop to communicate with his friend, Roy, as well as Carson and the rest of the launch team. Brian needs to stop the hacker during the launch. Ng begs Brian for it to not happen and appears distraught.
The launch seems to be going well. Ng walks in the room where Brian is working on all upset, while everyone else is relieved. Carson calls Brian to make sure the Chinese hacker is gone, which Brian took care of. Carson celebrates the rocket being in orbit. Brian soon becomes distressed himself, once he sees how upset Ng is. The king is also looking up at the sky.
Brian then gets an idea, which Roy reluctantly goes along with. Brian explains to Ng that he's having Roy send the biggest amount of sound into space, which when released, will compromise the rocket. Brian and Ng hold hands as the rocket is ruined and explodes. Carson is not pleased. Brian tells Ng to stay away from him, since he's radioactive now. Ng still tries to go after him, but he just repeats for her to stay away from him, especially since she is just starting and he is finished. He tells her it's over.
Carson is outside, singing the wheels on the bus. He tells Brian that he gets it, since he left Brian for dead in Kabul, and this is his revenge. Brian tries to tell him he can't buy the sky, but Carson tells him that he can't stop the future with such desperate acts, since he will just buy another rocket. He says Brian will just become a joke, and tells him his life will be very, very complicated.
Brian and Colonel Lacy are waiting to meet with General Dixon. Colonel Lacey explains it's best to let the general speak first, and tells him to just take whatever he says. The general tells Brian its all his fault that Carson pulled out, and that he set back their footprint in the Pacific by a decade Brian claims he saw weapons, but the general tells him he saw a philanthropic effort. The general tells Colonel Lacey he told him Brian would be bad. He also tells Brian to stay away from Ng, because the Air Force likes her, and so does Hillary Clinton apparently, for her salute.
Before she goes to fly, Ng is seen with a bumper sticker from the hotel.
While in her kitchen, Tracy tells Brian that he ruined himself to get a girl, and that he didn't even get the girl, who was a good one. She also think its bizarrely sweet that Brian got them a new Santa. She reads him a letter Woody sent her, which says not to penalize him for not being emotional, and that he hated how she changed when Brian came back to town, though he doesn't like to hate, since it's not good for his brain. He admits he's not the original owner of her heart, but he is the better owner. Brian jokes he liked him better when he was silent. Gracie walks in briefly to say she noticed the new Santa. She takes notice of Brian being there before leaving. The rest of Woody's letter says that Tracy calmed the fear in him whenever he walked in through the door. Brian says he likes the letter Woody wrote, and that he lacks that romance, and Tracy should go be with her husband. Tracy tells him to go be with Ng, the girl who lit up his sky.
Brian helps Mitch hang up his flag. Once he returns to the kitchen, he sees Woody walk in. Woody is still silent but subtitles explain that Woody knows Brian is Gracie's father and they hug. Brian says it's Woody's family and always has been, and that they all love with him. Woody asks Brian if he slept with his wife, which he did not, but he did sleep with Ng. Woody enthusiastically hugs him once more. Brian stands in the doorway while Tracy and Woody hug and kiss. She and Brian smile at each other with tears in their eyes. Gracie and Mitch also come in to greet Woody. Mitch says goodbye to Brian outside.
General Dixon and Colonel Lacey tell Brian that he is off the hook. Nobody knew the whole story, that Carson really did have weapons. The general will take all the credit for the exposure though. Carson is getting picked up and taken away by men in Japan though. The general tells Brian to let Ng go, since she is on her way, and for him to get lost.
Ng is outside the hotel in her uniform, ready to leave. Brian shows up and says he wants to know everything about her. She asks what he's still doing there and he just tells her wherever she's flying to come back, since he'll be waiting. As she counts how many words he's spoken to her, he tells her he loves her and calls her by her name, Allison. They kiss and he says he's staying. He sees that she still has that hat. He does have one more thing to do though.
At night, Brian goes to Gracie's hula class and stands outside, watching her dancing. She notices him and seems confused with him being there, and he just nods at her. She cries as she puts it together that he's her father. She dances for a moment more but then runs out to embrace him before going back inside to continue dancing.
During the closing credits, we see Brian planting along the Hawaiian nation.