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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
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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*

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