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Brooklyn, 1985. With the mob world as a backdrop, three life-long friends struggle with questions of love, loss and loyalty.

New Orleans, 1981. Sonny Phillips, just discharged from the Army, returns home. The only life he’s known is as a gigolo, working for his mother, but he wants to leave that behind. However, the job his Army buddy promised doesn’t materialize, and he can’t escape his past.

Sarah Huttington, recently engaged, goes home to Pasadena with fiancé Jeff for a family wedding. She hears a rumor that “The Graduate” (book and movie) are based on her family. Did her grandmother and her mom have flings with the same man just before her parents married? Is she a strange man’s child; does this explain why she doesn’t fit in? Was her mother happy? Is she too facing a loveless marriage? Where can she seek answers: her mother’s dead, her father’s a pleasant naïf. Ask her salty grandma? Better to ask the man in the triangle, the real Benjamin Braddock. With Jeff’s blessing, Sarah heads for San Francisco, looking for the key to her past and to her future.

An out-of-control speed freak (Schwartzman) is introduced his drug of choice’s creator (Rourke) by his dealer (Leguizamo). A massive three-day adventure ensues (with Fugit, Murphy, and Suvari in tow).

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.

Lester and Carolyn Burnham are on the outside, a perfect husband and wife, in a perfect house, in a perfect neighborhood. But inside, Lester is slipping deeper and deeper into a hopeless depression. He finally snaps when he becomes infatuated with one of his daughters friends. Meanwhile, his daughter Jane is developing a happy friendship with a shy boy-next-door named Ricky who lives with a homophobic father.

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?