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Wedding crashers opens with John (Wilson) and Jeremy (Vaughn) mediating a divorce between a couple and their lawyers. It sets the tone for the movie because it shows how they feel about love and marriage. Afterwards Jeremy and John begin planning the three week long wedding season.
There is a montage of all the weddings they crash, the lines they use to get the girls, dancing, and cake cutting followed by a montage of John and Jeremy bedding the (mostly topless) girls they have picked up at the receptions. John can't close the deal with his last girl because he forgets her name and is just tired of the whole act. She asks him if he is 100% full of $#!t or just 50%. He's hoping its just 50%
The crashing ends with John and Jeremy in front of the Lincoln memorial nursing a bottle of champagne talking about getting old, crashing weddings, and what else there is in life. John is tiring of it all, but Jeremy is not. So the wedding season is over and John is exhausted, but Jeremy wants to crash the wedding of Secretary of the Treasury Cleary's (Walken) Daughter.
John isn't going to give it his all at the Cleary wedding until he sees Claire (McAdams). Then he pours himself into the pregame warmup which includes Jeremy's research on the Cleary family and Sec Cleary's economic policies. During the service the bride and groom recite vows they have written themselves. The vows have a nautical theme and Claire can't keep from laughing, this only makes John more interested in her. During the service John and Jeremy bet on things like what scriptures will be read next.
At the reception John and Jeremy start putting their methods to work on the Cleary girls. John talks to Claire at the gift table and shows he has a knack for identifying the contents of the wrapped gifts. Then he dances with the flower girl and gets hit on by Mrs Cleary (Seymore). He then moves in on Sec Cleary and praises his economic policies. Sec Cleary, impressed, then invites John out for a cigar.
Meanwhile Jeremy is doing balloon animals for the kids and gets stuck making this huge bike for a nasty kid. Gloria Cleary (Fisher) then comes up and asks for one. Jeremy asks if she wants a car because he just made a lifesize stadium and doesn't have anywhere to put it. They agree to dance instead. Jeremy is a great dancer as it turns out and he gets noticed by Sec Cleary dancing with his daughter. Jeremy starts in on his "broken man with a horrible past" routine and walks away from Gloria as the dance ends. With tears in his eyes he says he wishes he could be stronger for her, but he walks away to the beach to get some air.
Back at the cigars with John and Sec Cleary, Claire comes up to tell the Sec he is needed elsewhere. Claire and John make small talk about love and marriage and Claire lets John read the speech she has prepared for the newlyweds. John bets her that no one will laugh at her jokes and he encourages her to speak from the heart. He ends up being right and Claire takes his advice after floundering in the opening moments of the speech. Only after the speech does John learn that Claire has a boyfriend Zach.
Jeremy has just finished his conquest of Gloria and she professes her love for him and that she was a virgin. Jeremy needs to get out of the reception fast but John wants more time with Claire. Gloria invites them back to their place on the shore and John forces Jeremy to go along. John is convinced he can win over Claire despite her boyfriend and everything works in his favor throughout the weekend. Everything starts going very badly for Jeremy.
Jeremy gets tackled hard twice by Zach during a touch football game and gets a cut on his leg. Gloria is fixing him up in a bathroom when he tries to make some room between them. Gloria starts spraying his wound with alcohol and crying that she was just a notch in his belt like her dad warned her. He tells her he just thinks they are expressing their love in physical ways when he doesn't really know who he is inside. This calms her down and she starts telling him about all the imaginary friends she had as a kid. As Gloria goes upstairs to get ready for dinner Sec Cleary basically threatens Jeremy.
At dinner it is revealed that Claire and Zach are going to get married sometime in the future, that Grandma is crazy, and that Todd Cleary is an artist who some think is gay. John puts eye drops in Zach's glass to make him sick. Mrs Cleary puts another move on John and makes him examine her new breasts.
That night Jeremy wakes up and he is tied to his bead and Gloria is sitting on top of him naked. She says that he wants space because she is not adventurous enough so she wants to fulfill all of his fantasies. She stuffs a sock in his mouth and duct tapes his face and proceeds to take him. Later Jeremy is woken by Todd Cleary. Jeremy is still tied to the bed and Todd starts proclaiming his love for him. Todd has painted a portrait of Jeremy naked except for fig leaf over his wedding tackle. Todd has to hide in the closet when Sec Cleary comes in and in the end Jeremy promises to spend time with Todd the next day as long as they don't have to play tummy sticks that night.
The next morning Jeremy is a wreck because he's had no sleep and John is still working out how to get Claire alone. John gets some time with Claire on a sailing outing as Zach recovers from puking his guts out all night long. Zach shows his true colors when he is sick because he starts yelling at Claire and being really sarcastic. He also calls in a favor from a buddy who knows a private investigator to look into the two brothers from New Hampshire, John and Jeremy.
After the sailing trip the guys go on a quail hunt and Zach causes John to shoot Jeremy in the butt. Gloria nurses Jeremy back at the house and she reveals that wasn't a virgin on the beach. She only said that because that's what she thought all guys wanted to hear. Jeremy can't believe he's been lied to, but it turns him on and makes him love Gloria. John tells Jeremy that he is going to tell Claire the truth, but before he can Zach announces the brothers are wedding crashers looking for sex.
Sec Cleary makes John and Jeremy leave and the movie skips forward a few months. John is a wreck and Claire won't return his calls or letters. John tries to sneak into Claire and Zach's engagement party but gets beat up by Zach. John goes over to Jeremy's house only to find out Jeremy and Gloria have been hooking up the whole time. John starts crashing weddings on his own and breaking all the crashing rules and making an ass of himself.
Jeremy goes over to John's to apologize and to tell John that he and Gloria are getting married. Jeremy wants John to be the best man. John says he will not go to the wedding. Instead John hooks up with Chaz (Will Ferrell) who invented the rules to wedding crashing. Chaz lives with his mom and has started picking up girls at funerals. John attends a funeral with Chaz and sees a widow crying. John realizes what it means to be without the person you love. So John decides to crash Jeremy's wedding for one final shot at Claire.
Jeremy and Gloria are getting married and Claire is one of the bridesmaids. John sneaks into the church during the service but slams the door on accident and since the Sec of Treasury is there, the secret service start roughing John up. From the front of the church Jeremy tells the secret service to let John in since he is the best man. Once at the front, John starts whispering to Claire that he just wanted to see her again. Claire starts to cry and walks down the aisle to get away, but John goes into a monologue about true love. He says that he's not asking Claire to marry him, only that he's asking her not to marry Zach. Zach starts yelling at Claire and in one of the best lines of the movie John says "now we all know what it will be like to be married to Ike Turner". Zach leaps for John but Jeremy knocks Zach flat. Sec. Cleary tells Zach that he put up with Zach's stories because he thought Claire loved him and Claire's happiness is what is important to Sec. Cleary.
All is well and the two couples drive off in a convertible. Jeremy says its just a suggestion but there is a really big wedding in town that weekend. John says they shouldn't crash it because they haven't prepared and don't have a back story. The movies ends with Claire saying they are a traveling folk singing group from Utah.
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