Disconcerting as the grin he then waited my pleasure with was the cast of his features, not just like any I had seen.

I do not perfectly understand "with was" -- with what? This is rather confusing for me.

I am not a native speaker.

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    Is this from something or did you write it yourself? This sentence is incorrect grammatically. There are many issues as a result. Also, wrong Stack. – Sora Tamashii Mar 16 '19 at 23:08
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    Questions about a sentence you read somewhere and do not understand belong on English Language Learners. It would be helpful to those who would answer you if you could provide the source of the sentence: where did you find it? – Galastel supports GoFundMonica Mar 16 '19 at 23:14
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    I found the source, and it seems to be neo-archaic speech. Poorly written garbage. From 1966: Giles Goat-boy, Or, The Revised New Syllabus – Sora Tamashii Mar 16 '19 at 23:14
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    The sentence is not grammatically incorrect, although it does use an unusual form. – David Siegel Mar 17 '19 at 4:31

The sentence would probably be better as follows:

He grinned disconcertingly then waited. My interest was held by the form of his features which just were not like any I had seen.

  • Okay, thank you. Your simplified version made me realize that "Disconcerting as the grin he then waited my pleasure with" is all together and I could find 'wait upon his pleasure' by Shakespeare. This is John Barth, his style is nearly perfect. I could not exactly break down the sentence, I should have associated 'wait with' right away. Sorry. – As Vet Mar 16 '19 at 23:18
  • No. You're fine. Just wanting to help as best I can. :) – Sora Tamashii Mar 16 '19 at 23:23

An alternate version of this sentence would be

The look of his features -- not just like any I had seen -- was as disconcerting to me as the grin he showed as he waited for my response.

The speaker makes clear that he is upset, mildly upset, by both the unusual facial features of his visitor and by the grin that the visitor showed. He equates these two sources of upset. The phrase "waited my pleasure with" is somewhat archaic, but in no way wrong. I would not imitate it in most writing, however.

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