Barry is a senior at the University of Central Florida, and he has a history of relationship problems with girls dating back to prom night at the end of his high school years. After being dumped by yet another girl he probably never should have been with, he becomes fixated on making a journey to visit the reclusive West Virginia Wizard. It turns out that the former girlfriend Barry blames for starting him off on a string of bad relationships has become an assistant to the Wizard.
Barry’s friends gladly join him on this road trip in the hopes that they can improve his mood. His friend Serena tags along, intending to make a film about their journey to meet the West Virginia Wizard. It becomes apparent that she has an interest in Barry that goes beyond friendship, and Barry is conflicted because he has never really been interested in nice girls.
The trip grows loonier along the way between their antics and series of strange experiences. Barry and the others also discover that they are being hounded by a competing group from campus that is also making a film about the Wizard. When they arrive at the Wizard’s camp, Barry has a change of heart as to who he should be blaming for his problems. It seems that the Wizard has been of great assistance to him although it is unclear even to Barry whether it was by magical means or mere common sense.