No worries, you’ve got it! 
I need to read each one fairly quickly so I can fit my other VN club in, that has almost triple the amount each week. 
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While Simon is talking about hope, here’s what gives me hope:
~5700 characters into chapter 9, ~5300 to go… 
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That took very long, but I finally did it!! Take that, chapter 9!
Chapter comments
I was a bit sceptical when Tyler suggested to also do the whole treasure hunt thing for our 3 side characters - I mean, he was lucky with Mia, but not everybody is into that, especially if you’re so mentally worn down like they are. But I was very positively surprised how thoughtful he went about designing it! (Although to be fair, it barely felt like a treasure hunt at the end, and more an excuse to get them to locations they will like, but hey! I’ll take it!)
And now, that being said, looking forward to going back to the main story!
Also, while I agree that our side characters are rather flat, I kinda like Holly. Joe is okay-ish. Ritapon… the less said, the better.
Questions
Chapter 9 script for context, if needed.
Is the second sentence “It seems it was mainly popular amongst elementary schoolers.”? There are a few other variants that I considered, but this one seems to make the most sense to me.
“If noticed, Mia was squeezing Tylers hand tightly”? What’s that first part?
How would you translate that last sentence by Holly? I’m tripping over that “そういうことになっていた”.
I have a bit of trouble with those two sentences by Tyler:
- 楽しみがなく、飽き果てた、なんて言葉はな。
- “Without enjoyment, weariness something something, something something.”?
- And why does it end with “はな”? は + ない?
- 宝探しに飽きてから言って欲しいぜ！
- “I want you to say [it? what?] after you get tired of treasure hunting!”?
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I don’t feel 100% sure either, but I that was also my interpretation.
I’d say that is more like “when she realized, Mia was squeezing Tyler’s hand tightly” - as in she had done this kind of unconsciously. I feel there is some chance of this being “when Tyler noticed”, but I feel the は making Mia the topic points otherwise…
I’d break it down like this:
いつの間に => at what point
そういうことに => that kind of thing
なっていた => became / turned?
でありますか => just Holly’s quirky way of speaking, probably.
So basically she’s wondering how had Mia turned like that (in relation to being so close to Tyler) - そういうこと is basically standing as the place holder for the fact that Mia and Tyler are close. “Wait, what?! That Mia-chan, when exactly did you she turn like this!?”
Not confident on these ones.
My understanding is that は is simply making “言葉” the topic here. I feel the sentence is just being said in disorder due to it being informal speech. な is just the normal sentence ender な seeking confirmation.
飽き果てた. Here 果てた is used as an auxiliary verb to say something has been done completely or utterly (see meaning 3 in jisho). So here it would mean doing something to the point it’s utterly boring.
“It’s not fun”, “did it until absolute boredom”, those are some (heavy) phrases, aren’t they?
The “heavy” is just something I added from context, but there could be other interpretations - it’s just that Tyler is emphasizing those particular phrases / words.
宝探しに飽きてから言って欲しいぜ
I believe this is Tyler taunting them to say those phrases from the previous sentence but in regards to 宝探し - in the sense that he believe it’s impossible for them to actually get bored of it. “I want to hear you say (that) after you get bored of treasure hunting”.
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