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When diagramming the sentence, "Simon, would you please sing now?", should I diagram Simon or you as the subject? Would you be diagrammed as pronoun and please as an interjection? I am trying to help my son diagram real-life sentences and am getting stuck myself.

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Simon is a vocative, which could be suppressed.

The rest is an infinitive proposition, with "you" as the subject.

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    @Melissa: additionally: I'm not into diagramming sentences, but 'please' here is a pragmatic marker (a politeness marker, along with 'kindly' when used in a similar way). Pragmatic markers are 'taken to be separate and distinct from the propositional content of the sentence' (see PRAGMATIC MARKERS: Bruce Fraser). Although not always 'added words or phrases etc', where they are added words etc (eg please here), pragmatic markers are probably best considered to be outside the matrix structure of a sentence in the same way as parentheticals. – Edwin Ashworth Oct 9 '13 at 16:51
  • The sentence without the vocative is a yes/no question with you as the subject. Please is an adverb -- it happens to be a pragmatic particle, but it patterns as an adverb syntactically -- and sing is indeed an infinitive, but it's the infinitive form that's required after the modal auxiliary would that is inverted with the subject you. – John Lawler Oct 9 '13 at 18:37
  • You have to select the patterns you need to bolster this model. *'Would you very please sing./?' // *'Would you sing(,) very please./?' *'There she sat, singing please.' I'll be glad to see a move back towards accepting a reasonable contribution of semantic (and the inclusion of pragmatic) requirements for word-class determination. – Edwin Ashworth Oct 9 '13 at 19:25

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