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Movie with Orion Slave girl

AC37

Cadet
Newbie
Hello all. I'm trying to remember a movie I saw at least 15 years ago at this point and I'm coming up with bupkus with Google searches and it's driving me nuts. All I can remember at this point is that the main character, a young-ish (under 40 but over 16, if not more like his 20s or later) man had a strained relationship with his girlfriend in no small part because of his love of Star Trek, and at one pivotal moment related to this he shouts at her words to the effect of, "...and I live in the xx (23rd or 24th) century, I'd live in the (24th or 23rd) century!," obviously referencing his preference for TOS over TNG or vice versa, and that overall Star Trek and his love of it was a major element of the movie.

The only other detail I can remember is that they have a party later in the movie, and a girl shows up dressed/painted like an Orion slave girl, who I think dances for everyone, who he later talks with and maybe even ends up getting into a relationship with?

This movie can't be any more recent than 10, if not more like 15+ years ago, and maybe longer than that. I'm also pretty sure it was produced absolutely no earlier than 1990, but I think more precisely it was produced more like mid-late 90s.

I know this isn't much to go on, but I suddenly found myself wanting to watch it again the other day, but remembering almost no details about it I'm having absolutely no luck in finding it.

Thanks much for your help!
 
Free Enterprise is the name of the film. William Shatner is in it as himself.

Directed by the great Robert Meyer Burnett, and supposedly based on him and his group of friends navigating singles' life in 1990s Hollywood.
 
I had my tongue firmly in my cheek when I made that statement. It does make for a very interesting rewatch knowing what will become of Rafer Weigel's character in the Free EnterpriseVerse. Not that I ever intend on rewatching that movie anytime soon.

There are like 600 "single white guy has dating problems" movie made in the 1990s, and the only thing Free Enterprise has going for it was that the Single White Guy was a bit of a sci-fi nerd. Oh, and William Shatner showed up.
 
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