The film opens with a middle-aged woman on a speedboat that’s flying over the water. Then Matt King (George Clooney) begins a voiceover about how all his friends who live in the continental U.S. think that living in Hawaii is all fun, all the time. He says they’re wrong, and we see he is sitting in the hospital at the bedside of the woman in the boat, his wife Elizabeth (Patricia Hastie), who is in a coma.
Matt is currently in the middle of another family matter as well he and all of his cousins have been passed down the deed to hundreds of acres of land in Hawaii, and it’s time for them to make a decision. If they sell, they’ll all split millions of dollars. The majority of the cousins want to sell, though there is one or two who want to keep the land in the family. The final decision comes down to Matt, who is the main titleholder. He says he’ll do whatever the majority wants to do.
At a meeting with his wife’s doctor, the doctor tells Matt that there is nothing else they can do for his wife. Now the decision rests on him as to when to pull the plug. He suggests that Matt go around and tell all of his wife’s friends, so they can say a proper goodbye. Matt goes back into his wife’s hospital room, where their friends Kai and Mark (Mary BIrdsong and Rob Huebel) are visiting. They ask if there’s any news, and Matt doesn’t tell them, he just says it’s more of the same.
Matt has two daughters, nine-year-old Scottie (Amara Miller) and 17-year-old Alex (Shailene Woodley). Alex is at a boarding school on another one of the Hawaiian Islands. Matt takes Scottie out to dinner one day, where they run into Elizabeth’s boating instructor (Laird Hamilton). He was with her on the day that she had her accident and was thrown from the boat. Scottie runs off in tears, and Matt pretty much tells him to go screw himself, as his wife wasn’t supposed to be driving the boat on her own. He runs after Scottie and suggests they hop on a plane and go over to the island where Alex goes to school to surprise her.
When they get to the school, it is nighttime and the dorm director goes to take them to Alex’s room, but she isn’t there. Her roommate says she thinks Alex went to the backyard. They go back there and find Alex and another girl drinking. Alex says hi to her dad without even trying to hide the fact that she’s drunk. The dorm director tells Matt that this is Alex’s last warning. Matt brings Alex and Scottie back home.
The next day, Matt is cleaning the pool while Alex talks on the phone. She says a male friend is coming over, and while Matt looks surprised, he doesn’t ask any questions. He tells Alex that he’s going to need some help with Scottie over the next few days. As Alex gets in the pool, he breaks the news that her mother isn’t going to recover. Alex slips underwater and breaks down where Matt can’t see her. When she gets out, he tells her that they have to tell all of her mom’s friends.
Later, in the house, Alex is still crying and Matt tries to ask her what she and her mother had argued about right before her mom got into the accident. Alex doesn’t tell him right away, but as he keeps pushing, she finally blurts out that her mom was cheating on him. She was out with some friends and saw her mom and a mystery man go into a house together. She confronted her mom and found out it was true. Matt is stunned. He leaves the house and starts running over to Kai and Mark’s. Once there, he demands to know whether they knew about this. They won’t give him a straight answer, and instead say he needs to talk to her about it when she wakes up. Matt finally tells them bluntly that she’s not going to wake up. Kai breaks down and gets angry at Matt for focusing on her infidelity when she’s going to die. Eventually Matt leaves and Mark follows him, telling him all they know is the man’s name Brian Speer.
Back at home, Matt meets Alex’s boyfriend Sid (Nick Krause) and the four of them go to visit his wife’s parents. Matt’s father-in-law (Robert Forster) takes the news stoically. He tells his wife that they’re going to go visit their daughter. His wife clearly has advanced Alzheimer’s, and doesn’t comprehend what he is telling her. Sid starts laughing, not understanding why she is acting this way. Matt’s father-in-law punches him. On the way back home, Alex yells at her dad to stop driving she sees a for sale sign in a yard that has Brian Speer’s picture and phone number on it. Once back home, Matt calls the number and leaves a message pretending to be someone interested in the house they passed.
Matt takes the girls to the hospital again and asks them to wait outside for a second. Once in the room, he yells at his comatose wife for making a fool out of him. Once the girls come in, Alex begins to do the same thing, and Matt stops her. He gets a call on his cell phone from Brian Speer (Matthew Lillard), who tells him that he’s going on vacation to another island with his family, but will be happy to show him the house when he gets back.
Matt decides to take Alex and Scottie to the same island Brian is vacationing on because as much as he hates him, he wants to give Brian a chance to say goodbye. Sid somehow negotiates his way along on the trip. One night in their vacation home, Sid and Matt have a heart-to-heart in which Sid says Alex doesn’t hate Matt, and she’s lucky to have parents when he never really had any.
They search the island for Brian with no luck, until one morning Matt is jogging on the beach and jogs right by him. He follows him back to a hut on the beach, where he is staying with his family. Matt realizes that these huts belong to his cousin Hugh (Beau Bridges), who he goes to visit. They discuss the two bids in for their land. The cousins want to go with one company over the other, since the other company wants to build a giant shopping mall. Matt asks Hugh if he knows Brian Speer, who’s staying in his hut, and Hugh tells him that Brian is a big investor in the company they want to sell the land to meaning by selling, Matt is effectively giving Brian millions of dollars in profit. Matt takes the group to go see the land, which is beautiful.
Matt takes the group back to the beach where Brian is staying, where he “accidentally” runs into Brian’s wife, Julie (Judy Greer). He works into the conversation the fact that they’re all from the same island. Later that night, Matt and Alex go to the hut and tell Julie that their family owns the hut and they’ve never actually seen the inside of one. Brian comes out and introduces himself, and Alex gets herself and Julie separated from Matt and Brian. Once they’re alone, Matt explains who he is and Brian says he didn’t want anyone to get hurt. Matt says Brian can come say goodbye if he wants, but it quickly becomes clear that Brian was just using Matt’s wife and didn’t even love her. On the way out, Matt kisses Julie. Matt and Alex leave, and the group flies back to their home island.
Matt’s cousins all get together to cast their votes on what to do with the land. The majority is to sell it to the company that Brian is a part of, but as Matt goes to sign the papers, he changes his mind. He knows that his cousins are going to be mad at him, which they immediately are, but he decides to keep the land even though there is some clause that says it will lose its value in seven years. But Matt says that means they have seven years to do something great with it.
Matt gets a counselor at the hospital to help him tell Scottie that her mother is going to die, since he can’t figure out how to do it on his own. Matt’s wife is moved to a new hospital room designed for those who are going to die. While sitting in the room, Julie Speer shows up, saying she knew something was up when Matt kissed her, and got it out of Brian after Matt and Alex left. When she knew that Brian wasn’t going to come say goodbye, she figured she would. She starts crying over Matt’s wife’s body, saying life wasn’t fair to either of them.
Matt’s in-laws come to say goodbye to their daughter. One by one, Alex and Scottie say goodbye to their mother. We see Matt, Alex, and Scottie in a small boat in the ocean, scattering her ashes.
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