Free Enterprise follows Mark (Eric McCormack) and Rob (Rafer Weigel), two guys in their late 20s who are emotionally stuck in adolescence: they're obsessed with science fiction, comics, and collectable toys, and they aren't especially graceful or successful in their relationships with the opposite sex. While both have actually been able to turn their obsessions into careers - Mark edits a sci-fi fanzine, while Rob works at a film production house - both feel the need for guidance as they approach 30. As children, they used to imagine themselves being counseled by William Shatner, whose role as Capt. Kirk on Star Trek elevated him to the status of a deity in their eyes. To their amazement, one day Mark and Rob meet Shatner in a bookstore and actually strike up a friendship with him, only to discover that he is just as confused about life, women, and work as they are.