Alan Jensen (Adrian Grenier) is attending Harvard University on a scholarship. He wants to experience as much as he possibly can mentally, physically, and spiritually. Alan is in the middle of a torrid sexual affair with Cindy Bandolini (Sarah Michelle Gellar), the daughter of a well-known Mafia kingpin. He also plays point guard on the Harvard basketball team. Alan is moving through life at full throttle and that's the way he likes it. He sees himself as invincible.
When his father and mother lose the family home in a tornado in the Midwest, Alan comes up with the idea of borrowing $100,000 from Cindy's father. She has even a better idea of having him make sure that the Harvard team loses to Dartmouth. He gets what he needs, and she makes a pile herself on a sure bet. Meanwhile, Alan keeps mum about all this with Chesney (Joey Lauren Adams), his twenty-eight year old philosophy professor who also happens to be his lover. Their pillow talk revolves around Wittgenstein and Jean-Paul Sartre.
Writer and director James Toback zeroes in on the Alan's grandiosity and his constant need to take risks and push everything to the limit. Traveling back to Boston after presenting his parents with the money they need to rebuild their lives, he takes three sugar cubes of Sandoz-quality acid given to him by a friend who wants him to experience something far out. While Alan is hallucinating on the plane, Teddy (Eric Stoltz), one of the advisors to Cindy's dad, tries to calm him down. It turns out that he's really an FBI agent. Returning home and still disoriented, Alan finds himself being pressed from two sides by the law and by some goons sent by Cindy's father to kill him.
There aren't many films about college students these days outside of the moronic comedies of studs trying to get laid. Toback convincingly depicts the foolhardiness of youth. He leaves us wondering whether the dangerous acid trip may have done some permanent damage to Alan's brain.