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You can't really expect Shinichi to act rational when he's not the type of human who does anyways(and yes, those rational humans who don't let their emotions get in the way do exist.).
He has shown time and time again that his morals and emotions constantly get in his way which prevents him from logically rationalizing actions. Expecting him to become more desensitized is something you would expect more in the middle or end, definitely not in the beginning. That's just who he is, a damsel in distress. A naive wuss.
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