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Tear Jerker: Hayate the Combat Butler
Both Hayate's reaction when he doesn't get into the school he wants and Athena's time sitting next to the Despair Event Horizon after her and Hayate's break up.
A little funny, but there's the time when Hayate tells Maria his dream...is to have an apartment. Not a particularly big apartment, either. Remember, this is not his goal, it is his dream. It is the absolute highest he will aim for. And when he misinterprets the shocked look on Maria's face, he says "Is...is it too much?" Dear lord, man.