Long Island, NY 1988: Just before her wedding, the bride and her bridesmaids are primping and talking. Once her sister-in-law leaves the room, she makes fun of how ugly she is with the other bridesmaids. She also tells them that she slept with another hot guy the night before, and swears she’ll try to stop once married, but since her husband “has a zucchini in the middle of his face”, it will be hard. She says she’s marrying Danny (Adam Sandler) because he is going to be a cardiologist, but she isn’t in love with him. She had no idea that her fiancé was outside and heard everything.
Next we see him in his tux at a bar, with his HUGE nose, drinking and heart-broken, at having called off the wedding. A gorgeous girl (Minka Kelly) comes in for a drink, and is hit on by every guy in the bar. Mistakenly, she thinks Danny is another smarmy guy, but when she sees his wedding ring and hears his sad story, she feels terrible for him, and tries to make him feel better. She asks him to her place, and after a night of great sex with a hot girl, Danny has an epiphany: he switches from cardiology to plastic surgery, gets his big nose fixed, and realized that he can keep from getting his heart broken again by just pretending to be married, and having sex with hot girls.
Today: Dr. Danny Maccabie is a successful plastic surgeon in Beverly Hills. His loyal assistant is Kathryn Murphy (Jennifer Aniston), a single mom of two. She is frazzled with juggling it all, and doesn’t pay much attention to her appearance. While seeing a patient with a botched eyebrow lift (Rachel Dratch), his cousin and best friend Eddie (Nick Swardson) comes in. He also is a patient of Danny’s: he had a penile enlargement. Danny still picks up girls by pretending to be in a bad marriage, and wears his fake wedding band.
Later that evening, Danny and Eddie go to a swanky party at a beachfront estate. The host, Adon (Kevin Nealon), is a friend of Danny’s. He has had so much plastic surgery that his face doesn’t move. A kid at the party slips and falls, and Danny gets his medical bag and stitches up the wound. He meets Palmer (Brooklyn Decker), a gorgeous 23 year 6th grade math teacher. She and Danny talk, and walk to the beach, and kiss and spend the night. In the morning, they both feel that they have something real going on, and she wants his phone number. While reaching in his pants pocket for his card, she finds the fake wedding ring, and is furious that he is married. He can’t think of what to say, and she leaves.
At work, he discusses the evening with Kathryn and she is disgusted with his fake wedding scenarios. He can’t figure out how to tell Palmer the truth, and comes up with an idea: he’ll tell her he is getting divorced. He goes to her school with flowers, but before he can say anything, she dumps the flowers in the trash. He explains that he IS married but about to be divorced any day. She accepts this on one condition: she needs to meet his first wife, “Devlin”. Danny goes back to the office and gets Kathryn to pretend for him. Kathryn and her kids have adopted the word “Devlin” to substitute for “crap” as in “I have to take a Devlin”, in her obvious dislike for a frenemy named Devlin from her sorority in college. It was the first name that popped into Danny’s head, and so Kathryn has to pretend to be “Devlin Maccabie”. He takes her shopping to Beverly Hills, as he says she needs to look like a plastic surgeon’s wife. After stops at Barneys, YSL, Tiffany, Chanel, and a hair salon, Kathryn is ready to be his “hot first wife”.
Palmer and Danny have a drink while waiting for Kathryn, and heads turn as a stunning woman in a white dress, heels and blonde hair waltzes in-it’s Kathryn, all decked out, playing the part. As they talk, she makes a put-down of Danny, and he follows: he has ED, she has a problem with pills, he has irritable bowel syndrome, etc. All goes well until they are saying goodbye: Kathryn’s phone rings, and she answers it. Her son is calling to complain that his sister is selling his stuff on Ebay again. Palmer hears the conversation, and asks, “You have kids?” Kathryn realizes her mistake, panics, and leaves.
A day later, Danny takes Kathryn’s kids (and nanny) out for pizza and brokers a deal with them: they will pretend to be his kids for a day if they each get something. The older daughter, Maggie, wants cash and acting lessons. The son, Michael, wants to go to Hawaii to swim with dolphins. He settles on video games and unlimited tokens at J.D. McFunnigan’s, a kids’ pizza-place that their dad was supposed to take them to, but never did. Kathryn is not happy with the situation, but reluctantly agrees. They agree to all meet Palmer at J.D. Funnigan’s.
Kathryn and kids show up, and Kathryn looks amazing, dressed in heels and a slinky black dressshe’s just playing the part. Brooklyn likes the kids, and while talking to “Bart” (Michael) he says that he is sad because his dad canceled on taking him to Hawaii to swim with dolphins because of her. She is aghast, and Danny quickly recovers and says they are all going…and glares at Michael. Michael and “Kiki Dee” (Maggie) smile-they got the best of Danny and now he has to take them all to Hawaii.
At the airport, Kathryn’s boyfriend unexpectedly shows upit’s Eddie, pretending to be “Dolph Lundgren”, the sheep shipper. He wants to go, too. At the hotel, they get suites, and spend the day at the beach. Danny even takes a few minutes while with Eddie to look at engagement rings-he thinks that Palmer might really be the one for him.
At dinner, “Dolph” is so obnoxious, that Kathryn leaves. She wants out of the deal and has had it with the whole charade. While talking to Danny, she hears someone call her name: it’s Devlin Adams, the mean girl from college. Devlin (Nicole Kidman) is with her husband, Ian (Dave Matthews), who invented the iPod. They are wealthy and obnoxious, and Kathryn tries to get away, but not before making Danny pretend to be her successful husband. They get stuck agreeing to have dinner with Devlin and Ian the following night. Danny has saved his charade, as now Kathryn needs him to be her fake husband, and it is even.
In the morning, Palmer has signed them all up for a day of hikes, climbing and exploring; Danny is disappointed as he wanted to spend the day alone with Palmer. The whole group of them goes and end up at a gorgeous secluded waterfall. Palmer takes off her clothes to swim in her bikini. Danny and Eddie just stare. After a minute, Kathryn decides to go also, and strips down to her bikini…and they stare again at the two hot women. It is clearly the first time Danny has ever thought of her as a “woman” and not just a friend and employee.
That evening, Palmer offers to take the kids so that Dolph and Kathryn can have a romantic evening. They order room service and play games, and have fun together. During one of the games, Bart says he’s sad because his dad never has time for him, and Palmer glares at Danny and leaves. Danny knows that Bart meant his real dad who is a dead-beat, but Palmer doesn’t know that, and thought it was about Danny. He tells them to focus, and they fake hug, laugh, and Palmer sees this and feels better.
So that they can spend more time together (after what Bart said), Palmer arranged a spa day for her and Kathryn, and Danny has to spend the day with the kids. He takes them golfing, where they pose for fake pictures that look like they are having tons of fun together. Then they plan the dolphin-swim, but Bart tells him he doesn’t know how to swim. Danny asks, “What, you were going to walk with the dolphins?” He tells Bart he will teach him to swim. Eddie, Danny and Kiki Dee work with Bart, and as he swims the width of the pool for the first time without floaties, his mom and Palmer arrive and see his accomplishment. Both Palmer and Kathryn beam at Danny, and he smiles at both, and is feeling conflicted as to which woman he really cares for. Devlin comes over-realizing that Palmer thinks Kathryn is also named Devlin, Eddie shoves Palmer in the pool before she can say anything. Devlin reminds them that they are having dinner together, and before Palmer gets out of the pool and realizes the situation, they quickly agree.
Eddie takes Palmer out for dinner, to supposedly get to know her, while Danny and Kathryn go for dinner with Devlin and Ian. Devlin is a show-off, constantly talking about money and trying to one-up Danny and Kathryn at every chance. There is a hula contest, and Devlin goes up. Kathryn has no interest, but when Devlin quips that this “isn’t her thing”. Kathryn throws back a few shots, and takes her on. The two come out in bikini tops and hula skirts and have the contest. All are eliminated except Kathryn and Devlin, and the competition heats up--clearly, Devlin is taking this quite seriously, and Kathryn is determined to not let her win. It ends in a tie, but Devlin insists on a tie-breaker: it is the “Coconut Smoochie”. Each couple starts with a coconut in between their stomachs, and have to work it up to their lips, without using hands. Devlin is furious at Ian for dropping the coconut, and they lose, and Kathryn and Danny laugh, and nearly kiss when they win.
As they return to their rooms, they realize they have feelings for each other, but Kathryn needs for Danny to admit it first, and be ready to grow up and leave the young girls behind. They share a close moment and are about to kiss, when the kids hear them and come out. They say goodnight. Danny realizes that he has feelings for Kathryn, and leaves to go talk to her, and bumps into Palmer and Eddie returning. They had a good time, and while talking he told Palmer that Danny had been ring shopping. She puts him on the spot, and says why don’t they get married in Hawaii tomorrow? Eddie is happy, thinking this is what Danny wanted, but he has no idea that Danny was thinking about Kathryn. Danny says ok-wedding tomorrow. He calls Kathryn later, and she tells him he needs to decide. And, if he gets married after all, it will be too hard for her, so she is going to take a job offer she has and move to New York, and start fresh. Danny is sad, but understands.
Kathryn is drinking at the bar while Palmer is getting ready for the wedding. Devlin shows up and joins Kathryn. Kathryn fesses up to the whole scam-she isn’t married, is a single mom, and Danny is about to be married to Palmer. Devlin also confesses that she and Ian are getting divorced-he’s gay (he is at the bar, hitting on sailors). They realize they have much more in common than they thought, and should have been honest with each other the whole time. They hug and are friends. Kathryn tells Devlin that it’s hard to see Danny getting married b/c she thinks she is in love with him. Unbeknownst to Kathryn, Danny has been sitting behind her at the bar and heard everything. Devlin sees this and leaves. Kathryn asks him why isn’t he off getting married? Danny tells her that he was on the cliff overlooking the ocean about to start his life with the one he loves…and she wasn’t there. He tells her that “She’s not you”. He leans in and they kiss.
Michael got to swim with the dolphins, Palmer met a tennis instructor on the flight home (her real-life husband, Andy Roddick), and Maggie got to take acting classes from the real Dolph Lundgren. And, Kathryn and Danny got married, and he finally wears a real wedding ring.
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