Josh Parker and Tiffany Henderson are childhood friends turned high-school sweethearts, who try for a long-distance relationship as he goes to the University of
Ithaca and she goes to the University of
Austin. Josh becomes insecure when he cannot regularly reach Tiffany by phone. Fearing infidelity, he begins sending her videotaped messages. Josh asks his friend and roommate, Rubin, to mail his latest tape to Tiffany before leaving for his
Ancient Philosophy class. Josh's Ancient Philosophy professor tells him he needs a B+ on his midterm to pass the class. Josh's best friend, E.L., convinces Josh to stop worrying about Tiffany and notice the beautiful Beth Wagner. Beth is in love with Josh, much to the chagrin of Jacob, the self-absorbed Ancient Philosophy
T.A. who is obsessed with her. Later, E.L. throws a party where he auctions off several female students, including Beth. Scared of Jacob, she convinces Josh to outbid him. He and Beth escape to his room and record themselves having sex on his camcorder. The next morning, Josh tells his friends that he slept with Beth and recorded it. They immediately play his camcorder tape, expecting to see them having sex, only to find love letters and songs performed for Tiffany. Josh believes that Rubin mailed the sex tape to Tiffany. He then hears a voicemail from Tiffany saying that she has not called due to the death of her grandfather. With E.L. and Rubin, Josh asks
shy loner Kyle to tag along on a road trip to Austin, as they need his car, owned by Kyle's strict father, Earl. After leaving the interstate in
Bedford for what they thought was a "shortcut", they find a small bridge collapsed, realizing they will waste five hours backtracking. So, E.L. and Rubin convince them to jump the gap. Kyle objects, but they proceed. They make it across, but the car is wrecked, destroying Josh's philosophy textbooks. The group continue on foot, stopping at a motel. Rubin tries to buy
marijuana from the unsympathetic motel clerk, but is informed that Kyle's credit card is maxed out. Looking for transportation, E.L. persuades
blind woman Brenda, at a school for the blind, into letting him take a bus for 'repairs', and they resume the journey. After a series of misadventures, the group finally gets to Austin and Tiffany's dorm. Josh intercepts the tape, just as she arrives. Earl also bursts in, furious over the car and the credit card, threatening to drag Kyle back with him. Kyle finally stands up to him, stating that he is going back to school with his friends. Earl assaults him, and a mini-riot ensues. Josh and Tiffany retreat to talk, then Beth calls to warn him about his midterm. While he talks on the phone, Tiffany starts to watch the tape, which luckily is mostly Barry mooning the camera. She and Josh amicably break up. The group returns to Ithaca just in time for Josh to take his midterm – with a little help from Beth, who called in a bomb threat to delay the start of the exam. Josh passes the philosophy course and begins a relationship with Beth (happily making videos); Jacob eventually dies as a result of leading a cult staging a mass suicide, which no one but he carried out; Rubin becomes a successful marijuana cultivator; E.L., inspired by his sperm donation, begins dating a pre-med student; and Kyle starts dating Rhonda and reconciles with Earl. ==Cast==