Josh, played by Breckin Meyer, and Tiffany, portrayed by Rachel Blanchard, are a couple deeply in love, navigating the challenges of a long-distance relationship. After enrolling at the University of Ithaca, Josh is eager to keep the romance alive with Tiffany, now attending the University of Austin. They promise to call each other daily, but when Tiffany fails to reach out, Josh begins to worry that she might be seeing someone else. Unbeknownst to him, the real reason for her silence is the death of her grandfather. To express his unwavering affection, Josh decides to create a daily video blog addressed to Tiffany.
In one of these heartfelt blog entries, his friends, Rubin Carver, played by Paulo Costanzo, and Barry Manilow, acted by Tom Green, interrupt the video, leading to some comical moments. Barry's obsession with his pet snake, Mitch, becomes a recurring theme. As Josh prepares to send his latest tape to Tiffany, he's struggling academically, struggling with his Ancient Philosophy class. His friend E.L., portrayed by Seann William Scott, tries to encourage him to move on, particularly towards Josh's other friend, Beth, enacted by Amy Smart.
During a party hosted by E.L., an auction for the ladies ensues, with Beth being a prominent figure in the bid. With a nudge from E.L., Josh outbids Jacob, the teacher's assistant, who has a crush on Beth. After a dance, Josh and Beth decide to take their relationship a step further, recording their intimate encounter with the same camcorder Josh uses for his video to Tiffany. The next day, however, Josh's friends demand proof of his escapade, leading to a shocking realization; they inadvertently sent the private tape to Tiffany instead.
Receiving a voicemail from Tiffany reveals that her silence was due to family tragedy, prompting Josh to embark on a road trip to Austin to reconnect. Joined by E.L. and Kyle, played by DJ Qualls, who is paralyzed with anxiety due to his overbearing father, the group takes on the 1,800-mile trek. Comical misadventures ensue, including a failed attempt to jump a gap that results in the destruction of their vehicle.
As they navigate their journey through laugh-out-loud situations—from Rubin's attempt to score drugs at a motel to Kyle’s tense relationship with his father—tension mounts when Earl, Kyle’s father, discovers the group's chaos. Their wild ride to Austin is filled with unexpected twists, and once they finally reach Tiffany's dorm, the hilarity continues when Josh intercepts the tape sent to Tiffany. This tape turns out to be nothing more than Barry's foolish antics.
With the pressure mounting, E.L. reveals to Josh that he’s been tricked, and with only 48 hours left, he must hurry back to school or face failure. In a heartfelt exchange, Josh and Tiffany amicably decide to part as friends, focusing on their respective futures. Thanks to Beth's support, Josh makes it back just in time to take his midterm, ultimately passing and allowing him to pursue a fresh start with Beth as they continue to make videos together.
