My wife recently started to show an interest in watching Star Trek. Previously she had seen The Wrath of Khan when she was single digits in age and not much else.
So far we have watched some of the first season of TOS and some other key episodes (still need to show her Mirror Mirror and The Trouble with Tribbles for sure, and probably episodes with Pike, which I think is starting to come up for us soon).
We watched a few episodes of TNG, for some reason Paramount through Amazon started us in the middle of season 3 instead of the season 1. She did not like how Wesley is treated on the show (she is a huge fan of Wil).
From there we moved to Voyager and are about half way through the second season. She is liking it, but not a fan of Neelix (I cannot wait to tell her he improves after Kes is gone) because of his jealousy towards anything that interacts with Kes. I have never finished watching all of Voyager myself, I think I am in season 6 or 7.
I watched all of Discovery (I think I finished anyway), the first Season of Picard, most of Strange New Worlds, and some of Lower Decks. Since she has said she wants to watch the new stuff with me I am doing my best to not watch it all so I have some new episodes with her.
At what point would you move from the old stuff to the new stuff to keep someone from being too confused? Or if confusion arises would you go back and watch the old stuff to answer questions? I know we will not watch Picard until we have gotten well into the Borg stuff in Voyager and some episodes of TNG dealing with it.
Why not just go through it in order? Make the new stuff a treat earned for getting through everything else. I’d start with the TOS pilot and go forward. She’ll either like trek or she won’t, jumbling it up isn’t going to make her like it more, but it may make her like it less.
Don’t impose your preferences for doing things in sequence or being a completionist on new viewers please. This seems really bad advice and likely to turn off more potential fans than pull them in.
OP’s question is about how to figure out how to engage someone in the franchise who seems to have her own specific preferences, and things that put her off.
I’m a viewer who first saw TOS as a small child when it was in first run, and everything in first run after that. It for others, there’s a whole range of shows for different tastes, best to figure out which one suits someone’s tastes and pull them into the franchise with that.
When we wanted to introduce our kids to the franchise, we started with TAS, then curated episodes from the other series. Like many tween, Voyager turned out to be ‘their show’ and it makes sense that Prodigy is strongly tied to Voyager. Our kids have moved onto other Trek shows and other franchises as they’ve moved through their teens. TOS, DS9 & Enterprise remain shows that they’ll watch occasionally. But one can never say that they’ve not liked Trek.
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