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If you thought Rika's experience was scary, in the Suzumiya Haruhi chapter, Endless Eight, the group is going Groundhog's Day on the last two weeks of summer vacation. Sound's familiar? Rika suffered through just over 100 years. Nagato says they've been through those same two weeks 15,498 times, which comes out to 594 years and a little over 5 months. And she remembered every second of it. Small wonder she looks bored.
Asakura in the fourth episode alone is already scary. But, for the love of god, listen the way she says "You think it's a... joke? Huh. You don't wanna die? You don't want me to kill you?" Really, really creepy. And you just realize that behind that happy-go-lucky facade, there is nothing.
In The Movie, just when Kyon is starting to realize that something is very off about the world, he happens to turn towards the door just as someone walks in. There before him stands Ryoko Asakura, back from hell with a casual smile on her face. Kyon has never been so abjectly terrified before.
That's not even the worst part. Just as Kyon is about to shoot Yuki, Ryoko appears from behind, successfully backstabbing Kyon! And then she goes on about telling Yuki that she's there for her while touching her face in a...rather interesting way. And she was spinnin' around like a happy child with a bloody knife in hand. Yuki's expression pretty much explains all.