When does it get dark and/or anxiety inducing? First 2 (and a half) episodes seemed tame... ... in before someone says "oh, you sweet summer child" or something 
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Episode 7
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thanks Jared - bracing myself already heh
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I feel you man. I pretty much had to go back and watch your Asagao Academy playthrough after I was done with this game. At least it's a cute visual novel where NOTHING BAD OR WEIRD EVER HAPPENS IN IT.
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YO I DID THE SAME THING. And then I had flashbacks to the Jacques route and had to just get off Youtube for a while.

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Heidi and Jared's wholesome reactions were a great palette cleanser after DDLC
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Gosh, it warms my heart every time! Especially after a messy experience like this...
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If ever I feel down, I just go and watch the hilarity that is Asagao Jared's secret being revealed That was heckin adorable
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What am I supposed to be noticing?
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It's the image of sayori hanging herself in the background zoom in and you'll see it better
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Oh dear God!
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Now to wait for the sequel.
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Actually what would be cool is if they made a sequel that was a non-scary dating sim in the vain of asiago academy. You would just waiting the howl game for something to happen and every know and then something slightly creepy will happen or be said and you would be on edge.
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If I could, I would just make a silly non-scary RPG involving the 4 girls and your main character. And Monika is forced to be the villain of the game as payback for messing with them in DDLC, lol. (thus, plenty of references of that game)
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This is one of the best Let's Plays that you have had on your channel so far; I was getting chills from it as well. I hope that, following in the footsteps of DDLC and Asagao, that we see more visual novels on the gameplay channel. They suit your commentary style, imo.
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