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Does the sentence "Can I not try that?" mean:

  1. I want to try that but I'm not allowed to
  2. I don't want to try that
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    It's ambiguous. But neither of your interpretations are likely. I would say it more probably means one of two things: (1) Am I allowed to try that? (2) Am I capable of trying that? Or, in its negative phrasing, Are you saying I'm not (allowed / able) to try that? Commented Jan 13, 2019 at 3:48
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    I automatically read it with an emphasis on "not," and so I interpret it as a sarcastic way to say, "I don't want to try that." Ex. Person 1: "Look, they're bungee-jumping." Person 2: "Can I try that?" Person 3: "Uh, can I not try that?"
    – Tommy Tran
    Commented Oct 10, 2019 at 8:15

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"Can I try that?" would be a simple question. "Am I allowed to try to do something?" Modifying try with "not" implies a slight fear that permitting the action might violate a formal or informal rule, or that the requester might lack the ability to successfully perform the action.

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