Just finished Angel Beats.

Fireworks

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Man, :'( I didn't cry. But that was the closest I've come to crying from an anime yet. The ending plot twist was like.... OMG , I felt it in my gut.

If someone can suggest an anime that actually makes me cry I'll pay you. But word to the wise I don't really cry, I didn't even cry when my grandmother died. :/
 

Conan

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You should watch Clannad and the Clannad after story if you want to cry.
 

Ushio

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Conan said:
You should watch Clannad and the Clannad after story if you want to cry.

I'll go with this guy, Ano Hana would be another teary eye'd suggestion
 

Conan

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In addition to what @Pun said, if you read, you should also read the Elfen Lied manga.
 

Beats

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WHY THE FUCK IS MY NAME IN THE FUCKING TITLE?!?!?!