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Bokurano have a lot of tragedy, but it focused more on the story than the tragedy itself... so it probably wouldn't make you cry. Maybe a bit teary at the end, but not cry.
Vampire Princess Miyu also have a lot tragic events, esp. the ending.
Bokurano, although it involved robots, the story itself for me is one of the most realistic out there (in terms of if you got into their situation, this is probably the way you would act).
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