Is the following sentence grammatically correct?

I like how when Katy asked "Is everything okay?", Lilly asked "Is it not?".

  • I like the way Katy asked..... – user66974 Feb 5 '16 at 8:24
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    It's comprehensible, at least. I'd consider it colloquial but grammatically valid. – Lawrence Feb 5 '16 at 8:49

Yes. In this case how is roughly interchangeable with that, and while maybe a little clunky, the phrase is grammatically correct. In this example there's no clearly superior way to phrase it (that I can think of) other than "I like how..."

EDIT: Here is why I consider how and that roughly interchangeable in the OP's sentence: Simply put, swapping one for the other has no impact on the sentence's logical flow or meaning. Either way, the causal relationship between Katy's question and Lily's reply is clearly established, and that's the role "I like how/that when" is intended to fulfill.

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    I don't think how is interchangeable with that in the Original Poster's sentence. Can you elaborate on the reason why you think how is roughly interchangeable with that? – user140086 Feb 5 '16 at 9:30
  • @Rathony See this post here or this one here. H&P class how as a subordinator (like that) when used this way. – Araucaria - Not here any more. Feb 5 '16 at 13:14
  • +1 from me. There's a lot of evidence that how like the word that is a subordinator here. – Araucaria - Not here any more. Feb 5 '16 at 13:30
  • @Araucaria If you contrast "we discussed how London was such a rubbish place to live" with we discussed how rubbish a place London was to live, I am not sure if you see any difference? If you contrast both of them with "we talked about the fact that London was a rubbish place to live", what is your thought? – user140086 Feb 5 '16 at 13:31
  • @Rathony Your first sentence is ambiguous between how being an interrogative word and a subordinator - but your second is an subordinate exclamative clause :-) The embedded clauses in the first one could be London is a rubbish place to live or London is a rubbish place to live in these ways. The third is How rubbish a place London is to live or How rubbish London is to live in. – Araucaria - Not here any more. Feb 5 '16 at 13:37

On the surface the phrasing feels redundant. However it falls in line with similar colloquial gems such as "also too" and "I know, right?" (The latter being a debatable case of reverse redundancy). As cumbersome as it is on the ear of a lingual enthusiast, it is a difficult one to argue based solely on grammar. Its widespread use is the single factor that makes it a battle best left unfought.

  • It does't seem redundant to me. "I like how Katie asked..." would mean something entirely different, and "I like when Katie asked..." is maybe grammatical, but feels too abrupt to me. – herisson Feb 18 '16 at 8:21

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