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Are nested conditions possible and grammatically correct?

  • I would have told you about the party if I knew you would have come if I had told you Lucy would come if you came.

Or something like:

  • Would you know, hadn't I told you that if I hadn't given you the papers, hadn't I taken them from John, that if I didn't have them you wouldn't pass your exam?
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    This makes my brain hurt. – fixer1234 Mar 30 '17 at 20:24
  • "Buffalo buffalo buffalo Buffalo buffalo Buffalo buffalo buffalo." is also a technically correct sentence with an actual meaning, but it similarly isn't a construction that is useful for conveying information. (en.wikipedia.org/wiki/…) – fixer1234 Mar 30 '17 at 20:28
  • I'm curious. Why else does English need conditionals and if-clauses? – SovereignSun Mar 30 '17 at 20:30
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    If you speak to a native speaker, and if you use a sentence like that (or this), and if the native speaker is willing to correct you, you will likely hear them say something like "huh?" – Deolater Mar 31 '17 at 12:47
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    @SovereignSun I think the difference is that English tends to "unroll" the conditionals a bit more. We tend to make sentences like "If I had known that telling you that Lucy would come if you did would have been enough to make you come, I would have told you about the party." This is done more often in writing than in speech, because it is somewhat difficult (at least for me) to keep track of the logical structure of these sentences in English. Slightly off-topic, I wonder if Russian chess skill relates to the ease of expressing multi-step conditionals in this fashion. – Deolater Mar 31 '17 at 17:52
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Your first one is grammatically correct, but never ever write anything like that unless you are trying to make people's brains hurt, or for humour value or something. There are times you might want to do that, but they should generally be pretty rare. Better to use multiple sentences, or at least a more structured sentence than a chain of woulds and ifs.

The second one I can't actually parse easily, so I don't know whether it's valid or not.

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