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Jack is incredibly irritated about the holiday visit of his "identical" twin sister Jill, as he has to pick her up at 4:00am. Jack's patience is soon stretched increasingly thin. Jill's neediness and passive-aggressiveness is maddening to Jack, turning his normally tranquil life upside down. Jill ruins Thanksgiving dinner by talking loud, calling one guest homeless, then running away into the woods with her pet Cockatoo. Jill has a list of things she wants to do -- be on a game show, go horseback riding, and do a studio tour. She has an open-ended plane ticket and decides to stay until the end of Hanukkah.
Jack's agency client, meanwhile, wants him to somehow get actor Al Pacino to appear in a Dunkin' Donuts commercial. Jack isn't sure how he's supposed to make that happen. Jill tries online dating, but doesn't get much of a response until Jack poses as Jill and alters her profile, leading to more than 100 responses. When her date, "Funbucket", meets her, however, he hides in the restaurant bathroom.
Feeling guilty, Jack takes her to a Lakers game where Pacino is supposed to be. Pacino pays little attention to Jack, but, amazingly, develops a crush on Jill. He gives her his phone number on a hot dog, written in mustard and ketchup. Jack is hoping Jill would leave by New Year's Eve, since the family is going on a cruise. Friends throw him a birthday party and extend it to Jill as well, having never known that he even had a sister. Pacino invites Jill to his home but she resists his advances and abruptly leaves. The next day, Jack's gardener, Felipe, takes Jill to a family get-together to have fun. Jack doesn't want Jill to be alone on New Year's, so he invites her to the cruise, and she gladly accepts.
A proposition is made by Pacino that he will do the commercial if Jack gets him a date with Jill. Jack disguises himself as Jill and goes on the date in her place. Jill starts to suspect that the only reason Jack invited her on the cruise is to persuade Pacino to do the Dunkin' Donuts commercial. When she phones Jack he answers as Jill, and then she hears Pacino, confirming her suspicions. Jack realizes how much he loves his sister and races back to the ship, but learns that Jill has gone back home to the Bronx. At a restaurant, there with a picture of the twins' deceased mother, she comes across a group of old classmates that used to make fun of her, led by Monica. They belittle her until Jack and his family show up. Jack and Jill speak in their made-up twin language, then Monica gets Erin in a headlock, but Jill saves her. Pacino also turns up at the party, dressed as the Man of La Mancha, to proclaim his love for Jill. She turns him down and goes home, where Felipe declares his love. She is overjoyed and embraces him.
The television commercial is made, with Pacino starring and singing as he promotes a new coffee -- Dunkaccino -- with a rap song. But when Jack shows it to him, Pacino hates it and tells him to destroy every copy and threaten those who have seen it.
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