There’s some guides for the “best” TOS episodes. Go find one of those and cherry pick in order.

Then restart TNG. The way Wesley is treated is character development for everybody.

All of DS9

All of Voyager

Then the newer stuff. I’d leave SNW for last since it’s still releasing episodes. Lower Decks you can do whenever, I feel like it’s easier to pick up and watch than the others.

I'm not too into the new showes as much as the older ones. I think Trek peaked with Deep Space Nine and Voyager, but this is just my opinion and many will disagree. Lol

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.

At what point would you move from the old stuff to the new stuff to keep someone from being too confused?

I don't think confusion is a big concern - if she has some basic familiarity with the franchise, it shouldn't take much more than explaining when the series is set. Beyond that, each show should stand on its own.

The only possible exception to this is "Picard," which is the most reliant on a previous series, but even then, the show should give the viewer enough information to watch it on its own terms.

When should you introduce her to the new shows?

After watching the old ones, of course!

Start with TOS, move on to the first set of movies, watch TNG, DS9 and Voyager, generations to nemesis, THEN you start on the new shows.

I mean, technically you could show in some kind of chronological order, but then she's going to be frustrated by the differences in technology. Especially discovery. They reeeeeally wanted to be more high tech than anything else while still wanting to be set before most things we've seen. IMO, it's very jarring and doesn't work well. But I just ignore the "it's before everything else" problem and it's a decent show.

I'm certainly biased, but I feel shows should be shown in the order they aired, not the order they're supposed to go according to Canon. They are a product of their time, for better or worse, and most issues I feel are more easily sidestepped if you view them as such, all together. Seeing the strings on the enterprise two episodes in a row is a lot easier when you don't have to compare it with ~~pike's sexy hair~~ modern cgi space battles.

I had this same question come up recently.

A friend of mine was out of town in a store that has a lot of entire series on BD or DVD (as well as movies of course), and he knew I was constantly referencing Star Trek, and he asked where he should start.

I didn't have much time to think since he was already in the store and had limited time. All things considered, I went with TNG as the perfect spot to start.

He's someone I used to work with a few years ago, and we play games together a lot. Knowing him (and just younger people in general), TOS would be so hard to watch with how dated it is. If not just the sexist and racist parts, then even for me it's hard to look at given how LCARS showed up and instantly made all the technology look immediately centuries behind.

But ever since then, it's looked mostly the same. At least until SNW and Disco. So I told him as much as I felt I could without boring him about where it's set in relation to the original show. 6 movies and 3 and a half series in, if I counted correctly.

But if he ends up being interested, I'll have him go through the other 2 golden era shows before going back for TOS.

Except I will have him watch the Tribble episode before he watches the DS9 episode about it.

He already had a small knowledge of it, the basic identity of who Kirk and Spock were, and the idea that it is a multi-show and many movie kinda franchise (I guess like a STU, which is MCU but for ST)

Ok I know people will say this is weird but watch through Star Trek Enterprise with Captain Archer since that was supposed to be a reboot for Star Trek that pulled in new fans. It explains the origin story of how humans got into space which I think helps a lot of newer watchers ground themselves in the universe easier. Make sure to make fun of it when it gets too absurd and always have a lighter nearby to hold up during the theme song.

Then go through TNG, Voyager and DS9 jumping between them every episode so you move through all three at the same time. I have been watching Star Trek with my gf this way and it is really fun to compare between the shows and it makes the bad episodes of any one particular series less exhausting because you get to take a break from that show.

Whenever you feel like it watch newer trek and catch up on it, I like all of it and some of it is really good.

Sprinkle in TOS episodes as you go, especially when there are direct callbacks to specific episodes (the SNW episode that echoes a TOS episode is a blast to watch right after watching the associated TOS episode they did such a good job).

I might not have even close to the same level of experience watching Star Trek as everyone else, but I think you can't go wrong with starting her on on TNG. My dad started me on TNG, and I've been a huge fan of it ever since. It's perfect for a new fan, since the show still makes sense even without watching the other series (though he has also shown me some of the original movies). And it lacks a lot of the sexism present in the OG series, which can be a turn off.

Though I found the first episode a little boring, it quickly got awesome as it went on. I've only watched that show and Discovery, but I'm pretty sure it will stay my favorite. The characters are likeable, Picard's a strong leader, and Data is a great foil for the rest of the cast.

I'd recommend release order because there are callbacks and crossovers, cameos, etc. that tie these shows together. You could watch the in any order, but you'd get more enjoyment out of picking up all the references and easter eggs. So, TOS -> (maybe TAS) -> movies 1 through 6 -> TNG -> movie 7 -> DS9 -> VOY -> movies 8 through 10 -> ENT. Then modern stuff like DSC, SNW, PIC, Prodigy, and LD.

That said, there's no need to watch every single episode of every show. Back on Reddit there were guides of "essential" episodes for each season of every series. Here's one for TNG. I'm sure you could find this for other shows too.