Josh (BRECKIN MEYER) and Tiffany (RACHEL BLANCHARD) have been friends since they were kids, and by the time they attended high school, that friendship turned into romance. Unfortunately, they decided to attend colleges nearly two thousand miles apart, but agreed that their relationship could survive such a distance and that they'd stay true to each other in an exclusive relationship.
E.L. (SEANN WILLIAM SCOTT), one of Josh's friends at New York's University of Ithaca, thinks that's a horrible idea and wants him to hook up with Beth (AMY SMART), a pretty coed who's more than attracted to Josh and needs a boyfriend to repel the advances of Jacob (ANTHONY RAPP), a creepy teacher's assistant.
Josh is reluctant, but when he can't get ahold of Tiffany and then hears from her roommate that she hasn't spent the past several nights in their room, he figures she must have dumped him. As such, he thus has a fling with Beth, a sexual encounter they record on video.
Although Josh feels like a new man the next morning, that only last a short while as he discovers, to his horror, that his brainy roommate, Rubin (PAULO COSTANZO), accidentally mailed that tape - instead of a sweet and syrupy one - to Tiffany. Things then get worse when he learns that Tiffany wasn't fooling around on him, but instead had left school for a few days due to the sudden death of her grandfather.
Realizing she won't return to school until Monday, Josh, E.L. and Rubin convince Kyle (D.J. QUALLS), a geeky and insecure student, to let them use his car to make a road trip to Austin to intercept the mailed tape before Tiffany returns and receives it. Leaving long-time student and campus tour guide Barry (TOM GREEN) to watch over Rubin's pet python, and taking Kyle with them, the students set off on their high speed quest.
With only a few days, a long way to travel, and Josh realizing he'll have little time to study for his crucial philosophy midterm given by Professor Anderson (WENDELL B. HARRIS JR.), the young men race across the country, not realizing that their high speed trek will lead to a series of near disastrous complications involving, among others, Kyle's father, Earl Edwards (FRED WARD), a testy motel clerk (ANDY DICK), a gross waiter (HORATIO SANZ), and even Barry's grandparents (ELLEN ALBERTINI DOW & EDMUND LYNDECK).