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If you liked School Days add

...then you might like Kuzu no Honkai add

Both focus on awry interactions of teenagers

If you liked Texhnolyze add

...then you might like Saishuu Heiki Kanojo add

Both are cyberpunk with depressing settings and partially-explained reasoning of how the story develops and how the story ends. The range of character sets and the context (high school life vs gang wars) are quite different though. But probably these two are the most similar anime on this recommendation list.