Danny Maccabee (Adam Sandler) is a successful plastic surgeon in Los Angeles who feigns unhappy marriages to get women, after having been heartbroken on his wedding day 20 years ago. The only woman aware of his schemes is his office manager and best friend Katherine Murphy (Jennifer Aniston), a divorced mother of two. At a party, Danny meets Palmer (Brooklyn Decker), a sixth grade math teacher, without his wedding ring on, and they have a connection together. The next morning, she ends up finding the ring, and she assumes he was hiding the fact he was married. She refuses to date him because her parents divorced due to adultery and doesn't want to be an adulteress herself.
Danny goes to Palmer's school to try to woo Palmer back. Instead of telling her the truth, he tells her that he is getting divorced from a woman named Devlin, named after Devlin Adams, whom Katherine had mentioned was an old college sorority nemesis. Danny informs her that they are getting divorced because she cheated on him with a man named "Dolph Lundgren" (not the actor). Palmer then insists on meeting Devlin, and Danny agrees. Danny asks Katherine to pose for him, and they go shopping on Rodeo Drive to buy her clothes, so she can look like a trophy wife.
At a hotel having drinks, Danny and Palmer are greeted by a made-over Katherine (posing as "Devlin"), who gives them her blessing. However, after hearing Katherine talking on the phone with her kids, Palmer assumes that her kids are Danny's as well, which Danny goes along with. Danny then privately meets with Katherine's kids, Maggie (Bailee Madison) and Michael (Griffin Gluck), to get them to play along. Initially, Katherine is furious, but she reluctantly agrees.
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