Free Enterprise (1998)

Synopsis
With a little help from the commander of the Starship Enterprise, two geeky sci-fi buffs venture into the final frontier -- finding a steady girlfriend -- in this satiric comedy. Mark (Eric McCormack) and Rob (Rafer Weigel) are 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 (though he does confess his burning ambition to produce a new version of Shakespeare's Julius Caesar in which he plays all the characters himself). Emboldened by his new friendship with Capt. Kirk -- wait, make that William Shatner -- Rob begins pursuing a romance with Claire (Audie England), a fellow sci-fi fan who is pretty, charming, and a few steps up on the maturity ladder from himself. But this is bad news for Mark, who isn't at all happy to be losing his best friend to some girl. Free Enterprise was the first feature for writer/director Robert Meyer Burnett and screenwriter Mark A. Altman, who freely (and rather bravely) admit that the lead characters are based upon themselves. ~ Mark Deming, All Movie Guide