What does the phrase "offensively knowing" mean?

Question

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?

MT_Head · Accepted Answer

"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.

Kim Ryan · Answer

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.

Packard · Answer

And "know" in the biblical sense means to "have sex with them".
https://kingsenglish.info/2011/01/24/knowing-in-the-biblical-sense/
“I knew her… in the biblical sense”, said the ribaldrous fellow with a wink and a nudge.
Many are aware that “knowing in the biblical sense” is shorthand for sex.  But few know what it is that’s ‘biblical’ about that ‘biblical sense.’
Well it all goes back to Genesis 4:1:
“And Adam knew Eve his wife; and she conceived, and bare Cain.”

What does the phrase "offensively knowing" mean?

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