My boyfriend knows absolutely nothing about the series other than that Natalie Portman is in the prequels. He wants to watch the prequels first - he likes her and is convinced you’re supposed to watch them in order.
I’m advocating Machete order (with pre-Special Edition VHS rips), but he really wants to watch Phantom Menace and I’m not sure where to put Rogue One/what other non-mainline material to include.
Do normies tend to like the sequels? I’ve told him upfront that I dislike them immensely, but I’ll tolerate them for him.
This may come across as ridiculous but please understand - I’m just trying to maximize my chance of a couples Han/Chewie Halloween costume this year.
Don’t watch the prequels first. It’ll spoil the original trilogy. Machete or release order would be good.
Once you’re done 1-6, watch the others at your own will. Solo, Rogue One, the sequels, any order (but watch the sequels in order).
If you really get into all of the above, check out the Clone Wars animated show (watch it in chronological order), then Rebels. I would recommend watching the live action shows after the animated stuff because they continue a lot of those stories, but you could do it either way.
In my opinion, the best way to watch ALL of it is to watch it in release order. Nothing gets spoiled, and everything gets built upon what we already know.