The movie starts with a little history of Danny Maccabee (Adam Sandler). 20 years ago, his heart was broken on his wedding day after he found out that his soon-to-be wife cheated on him the night before the wedding day.
20 years later, he became a famous plastic surgeon in Los Angeles. He goes around the city telling women about his unhappy marriage to get them fall for him. The only woman who knows about his trick is his office manager Katherine Murphy (Jennifer Aniston), a divorced mother of two.
At a party, Danny meets Palmer (Brooklyn Decker). Both of them connect instantly and they made love in the beach. The next morning, Palmer asked Danny for his number, so he told her to check his pocket for a business card but she ends up finding his fake wedding ring. He tried to explain but she assumed he was hiding the fact that he was married. She refused to see him again. Danny went to Palmer's school trying to too her back but instead of telling her the truth, Danny told her that he is getting divorced from a woman named Devlin. Danny told Palmer that Devlin cheated on him first. Palmer wanted to meet Devlin, so Danny asked Katherine to pose as Devlin.
On the day of the meet up, as they were about to leave, Katherine received a call from her kids. Upon hearing the conversation, Palmer thought that those were Danny's kids. Palmer wanted to meet the kids. Danny then paid Katherine kids, Maggie (Bailee Madison) and Michael (Griffin Gluck) to pose as his kids. When Palmer met the kids, Michael blackmailed Danny in front of Palmer to take them to Hawaii because he wanted to swim along with the dolphins.
At the airport, Danny's cousin, Eddie (Nick Swardson) suddenly showed up and disguised as "Dolph Lundgren", an Austrian Sheep Salesman and "Devlin's" love interest. While in Hawaii, Katherine reached her breaking point. As she pulled Danny aside and warned him to tell Palmer the truth, they bumped into the real life Devlin Adams (Nicole Kidman) and her husband Ian Maxtone-Jones (Dave Matthews). Devlin Adams was Katherine's old college sorority nemesis. Due to the old time rivalry between Devlin and Katherine, Katherine introduced Danny as her husband.
On a night when Danny and Palmer were spending time with Michael and Maggie, Michael suddenly broke down and complained that his real life dad didn't have time for him. Palmer got upset after hearing that so on the next day, Palmer asked Katherine out for a day at the spa so that Danny could spend some time with the kids.
On that day, Danny taught Michael how to swim. Katherine and Palmer witnessed with admiration on Danny winning the kids' hearts. On the same time, Katherine ran into Devlin who invited her and Danny out for dinner. Katherine asked Eddie to take Palmer out for dinner so that she and Danny could go out for a dinner with Devlin.
At the dinner, Devlin asked Katherine and Danny to tell each other what they admire most about each other. They ended up saying honest things to each other, with Katherine admiring Danny's sense of humour and Danny admiring the fact that he never had to lie to her.When Danny and Katherine got back to the hotel, they started to realise that they might have fall for each other. As they were about to kiss, they were interrupted by Maggie. So Danny headed back to his room.
As he was walking back to his room, Danny decided to go back to Katherine because his feelings for her was too strong but he ended up running into Palmer and Eddie. Palmer suddenly told him that they should get married the following day. Surprised by sudden suggestion from Palmer, Danny agreed to it. Katherine who was also on her way to find Danny walked into them and was shock by the sudden news. Later that night, Danny called Katherine and she told him that she would be taking a job in New York City.
The next day, Devlin ran into Katherine who was drinking at an outdoor bar. Katherine told Devlin the truth that Danny is not her husband and Devlin told Katherine that she is divorcing Ian because he is gay. Katherine also confided to Devlin that she was in love with Danny even though she knew that they couldn't be together. Suddenly Danny showed by behind her, telling her that he didn't marry Palmer and that he fell for her as well. Palmer headed back to the mainland alone. While on the plane, she met professional tennis player Andy Roddick who shared her interests. Sometime later, Danny and Katherine got married.
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