Damedol to Sekai ni Hitori Dake no Fan - Ch. 33 - This is Fun

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From the previous chapter, it's basically Kimiya's dad is the usual super strict Asian parent, who demands that he does everything perfectly and doesn't embarrass the family, while not showing any sort of affection or encouragement for his son.
@banneret

It's worse than that. His dad is saying that if he isn't perfect like his older brother then he's a failure. (His brother hates that.) All A's won't cut it. He has to be #1 in his class or else.
 
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He likes seeing her mess up and stuff, so when he compliments her clothes, its a bit funny to imagine that he likes them, too, because he thinks they're horrible and that she has horrible taste in clothing. (Especially considering the fact that her outfit's really good here.)

Actually, what if the reason he hasn't noticed her at his school is because he can't recognize her when she's not in constant-failure mode? Her clothes are normal and she's not doing anything too silly so he's just like "huh, that's a normal girl..."
 

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