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Hahah yeah first route experience is such a shock for any of the 5 routes. Though I get being fuzzy on that one part if you haven't had the context of the other routes.  It's actually Chase who killed Sydney. That's not a spoiler for the other routes either, you're supposed to find that out in Tj's.

I'd recommend playing Leo's next, then Carl's, then Flynn's and then Jenna.

Carl's is probably the most confusing to get through since it introduces a new idea that isn't explored in Leo's and Tj's so maybe playing Flynn's route before Carls would be better but either way I'd recommend you do Leo next and definitely end with Jenna.

wait wait wait, so, TJ saying he was the one who killed Sydney was just TJ trying to protect Chase?

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Don't you think it's a better option to do this order?
- TJ first, it barely has supernatural, it's the most chill and is good for "beginners"
- Then Carl's because it's kinda "separated" from the rest of the story and has a good horror ladder.
- Then Leo's, probably the scariest, introducing new elements to the story, but just briefly

- Then Jenna's, telling you even more about these elements introduced in Leo's story (also the dam scene is so good)

- Then Flynn, because it's the most complex, scariest (Sydney's flashbakcs), saddest, most wtf, and mostly because the very end of the route is like a twist: Within a few lines, you understand everything about the story, the past, the *truth*.

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I Think you could easily change places among Jenna and Flynn's route. I could tell Jenna's is the canonic good ending and Flynn is the canonic bad ending.