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Short for, "tell me when to stop". The grammatically improper, but obedient reply is, when. Some people who use this phrase are so pedantic about receiving an obedient reply that they will not stop if the reply is other than, "when", because they think it's funny.
Say when.

OK... That's enough.

I said that's enough!

Will you stop already?!?

When you say "when".

When, already! You've ruined my drink!!!
say when by Downstrike December 28, 2005
Words you can keep
What Tom (god) says (Tombstone)

Basically, this is a subtle nod to the famous epic movie of a spaghetti western namedTombstone, when the titular Doc Holiday says "Say when"
Tom: "Hey Dayveeitd."
Davit: "Yeah??????"
Tom: "I got a good one-uh."
Dayveit: "Okay...?"
Tom: "I'M DOC HOLIDAY Say When!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!" ;3
David: *walks awayuhn XD*
Say When by Hilfred Steelhelm May 30, 2020

What do you say when the cops come calling? 

I mean... If the send officer sexy then...
Hym "Sit on my face please? Ma'am- Er, uh- Officer? Can I request my last meal early? No? I'll confess immediately if you let me hit it from the back? You got me! I was conspiring to murder that pussy, baby! I'M GONNA SHOOT!!! My load in you...? What DO you say when the cops come calling? I mean, you know what they say: The cops can't come calling if you're coming in a cop! Uum... Do I fill out the paperwork BEFORE or AFTER I fill you... Out? Up? I donno... But yeah, one of those ☝️

When u say that ur fine, but ur not rly fine

When u say that ur fine, but ur not rly fine

smile when you say that 

(Western US via cowboy movies)

Your last remark crossed the line. Immediately retract/clarify/soften it, or I'll be offended/in your face/pumping you full of lead.
"Of course, there never was a man born in those parts who was worth a damn..."

"Smile when you say that!"
smile when you say that by Shane August 11, 2003

when you say that's so gay do you realize what you say knock it off 

-that's so gay
-When you say that's so gay do you realize what you say knock it off

When I say "jump" you say "how high?" 

The catchphrase of boomers in particular, possibly coming from the movie "Stripes" is a phrase that fuels their narccisim and the outcome being they wonder why their kids and grand kids go No Contact and abandon them or throw them into homes and abandon them.

The idea is you are supposed to question an order not act in blind subordenation. They just say "JUMP!" being confused you ask "How high and why?"

Boomers comically use the phrase "If your friend jumps off a bridge would you follow?" fueling more of their hypocisy.
"When I say "jump" you say "how high?"-Boomers

"Why do my kids hate me?"-Boomers
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Caleb knew the only thing to do after he didnt get prefect was take a failure shower.
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Acronym for Non-Athletic Regular Person. Your schools lacrosse team probably shouts it at you while you walk by.
Lookie at these bunch of narps, NARP NARP NARP
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He is high school liquid, he ate lunch with the nerds and hung out with the jocks after school.
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Purple Patch 

To describe coming into something good, coming into good luck and or good times.

Like walking over small green hills in the countryside then coming across a purple patch of flowers, thus it being unique and out of the ordinary.
I hit a real purple patch.

The other day this good thing happened unexpectedly then I was lucky with this, it was unique, I hit a real purple patch.
Purple Patch by Ralph Shitstorm October 27, 2020
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