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When a young man agrees to housesit for his boss, he thinks it’ll be the perfect opportunity to get close to the woman he desperately has a crush on - his boss’s daughter. But he doesn’t plan on the long line of other houseguests that try to keep him from his mission. And he also has to deal with the daughter’s older brother, who’s on the run from local drug dealers.

When “The Dude” Lebowski is mistaken for a millionaire Lebowski, two thugs urinate on his rug to coerce him into paying a debt he knows nothing about. While attempting to gain recompense for the ruined rug from his wealthy counterpart, he accepts a one-time job with high pay-off. He enlists the help of his bowling buddy, Walter, a gun-toting Jewish-convert with anger issues. Deception leads to more trouble, and it soon seems that everyone from porn empire tycoons to nihilists want something from The Dude.

Kathryn makes a bet that her step-brother, Sebastian, won’t be able to bed Annette (a virgin, who wants to wait until marriage) before the start of the school year. If he loses, Kathryn gets his Roadster, if he wins, he gets Kathryn

After their first year at college, the guys reunite for another summer of fun. Jim continues his quest for sexual independence by seeking the help of his old prom date, Michele, after an unexpected call from Nadia who plans to visit Jim. Meanwhile, Kev and Vicky find themselves in an awkward situation after having broken up for a year. Oz must deal with a long distance relationship when Heather heads off to France to study abroad. Old feuds die hard as the ever-so-horny Stifler harbors his hatred toward Finch, who is practicing the Hindu practice of Tantra.

Van Wilder is a guy who has been at his college for seven years. He spends most of his time throwing parties and “fund raisers”. When his father decides that it’s time for tough love, he doesn’t pay his tuition. So Van becomes a professional party thrower. At the same time, Gwen who writes for the college paper, is tasked with doing a story on him, but Van is too busy partying to do that. So she writes it using info from people who talk about him and writes an unflattering piece, which doesn’t make him happy. He then dares her to see if she can get the true story but is more interested in trying to score with her, which is not easy because she has a boyfriend, who is a snob, and who is not too happy with the amount time she is spending with him. So he tries to get rid of him.

At a high-school party, four friends (Jim, Kevin, Finch, and Oz) find that losing their collective virginity isn’t as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to try to be the first to “score.” And of course, the senior prom is their last best chance. As the fateful date draws near, the boys wonder who among them will get lucky. More importantly, do they really want to do it at all?