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Those four words roll off the tongue as a lighthearted way of asking "What's up? What's next?" And that tripping lightly stuff makes sense, since "How now, brown cow" has its origin in elocution, where the phrase was used to demonstrate properly rounded vowels.
Ron: How now, brown cow?

Paul: Not much. Just on my way to catch a movie with my girl.
by MoonCricket March 26, 2005
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Jun 23 Word of the Day
When a reply to a tweet gets more likes than the tweet it was replying to, usually indicating the unpopularity or stupidity of the original tweet
Damn you got 12 likes and his reply got 271 likes? He totally ratioed you bro
by FF29 July 06, 2020
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2
It actually means, "What's next?" I read that on the Merriam Webster Dictionary site after trying to look it up here.
"How now, brown cow?"

"You're going to turn into a purple cow."

*poof*
by Sara Harmon February 21, 2006
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3
lighthearted way of asking "What's up? What's next?"

Has its roots in prohition era referring to when a keg (brown in those days) was empty, "well, what are we gonna do now..."
"It seems as though the rave is over, Winnifred" says Penelope.
"How now, brown cow?" says Winnfred inquisitively
"Let's get poprox!"
by TexasCaveman July 31, 2005
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