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I just came across this phrase for the first time in 1984, book 2 chapter 4. The sentence reads (speaking of Mr. Charrington):

Nor did he seem shocked or become offensively knowing when it was made clear that Winston wanted the room for the purpose of a love-affair.

It also appears in Newton Booth Tarkington's Gentle Julia:

He wore a fully developed moustache, an easy smile, clothes offensively knowing; and his hair began to show that scarcity which Julia felt gave him distinction—a curious theory, but natural to her age.

I've never encountered this phrase before and can't find a definition online, though it is itself used in Wordsmyth's definition of "smirk".

Does anyone have a clear definition of the phrase?

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"Knowing" (definition 2b, Merriam-Webster), as an adjective, means that the person so described has inside information - one can give a "knowing look", a "knowing smile", etc.

To be "offensively knowing" means to give the impression of knowing a person's guilty secrets, and taking advantage of that knowledge to assert a higher level of intimacy or social status than would otherwise be acceptable (or pleasant).
A man who knows that a woman is having an affair might become "offensively knowing" and take liberties with her that he otherwise wouldn't dare to; a waiter or cabdriver who knows that his customer is doing something illegal might become "offensively knowing" and demand a higher tip (or give worse service) than usual.

  • This makes sense for the first quote, but what about the second? The phrase seems out of place there, describing a person's clothes. – Conman66 Aug 28 '17 at 1:39
  • I would interpret the second one as meaning that the clothes give their wearer an air of offensive knowingness - perhaps a slightly criminal appearance? I haven't read Gentle Julia, so don't know anything more about the man being described. – MT_Head Aug 28 '17 at 1:58
  • By the way - a friend once called me a "knowing fuck-it-all", which I still think is one of the best things I've ever heard. – MT_Head Aug 28 '17 at 1:59
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I would read it as that he took offensive after knowing this fact. It's a bit convoluted but I think the meaning is clear. Nothing wrong with an original coupling of words.

  • It doesn't seem to be original to Orwell, because I found an earlier instance of it, which I just added to the question. – Conman66 Aug 28 '17 at 0:49
  • There are many, many earlier instances - just take a look at Google Books. As always, don't trust the dates as listed; click through to the scanned image and take a look at the front matter to get a more reliable publication date. – MT_Head Aug 28 '17 at 2:38

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