A
Amaris
Guest
I would suggest if you are talking about someone under 30 who has never seen any form of Star Trek at all, start with the movies 1-6, then graduate to the fan collectives, then Movies 7-12. If you start them off with Star Trek 2009 and STID, I personally think you risk them rejecting the rest of Star Trek.
Besides, having someone think of Chirs Pine as the true, definitive Kirk is just, well, wrong. He's a fine actor, but Shatner IS Kirk. :P
It worked for one of my friends, though. She watched ST09 and practically begged me to unleash my Trek knowledge on her, and now she's a big fan of TOS. She loves it because the stories are fun, and she finds it "charming."

I precede the episode viewing with a lecture on miniatures, models and stop action. Then a lecture on editing where I select an episode which functions on parallel editing like the "The Doomsday Machine." We view the episode from the Blu-ray set. I conclude with a supplemental discussion using examples of the original model animation. The young trekkers love to participate in the discussion where they discuss everything from acting styles to the cold war.