The bigger the boat, the smoother the sailing.

A response to the phrase "it's not the size of the boat, it's the motion of the ocean".

Implies that "size matters".

Woman - "Wow dude, that's a really below average penis."

Man - "It's not the size of the boat, it's the motion of the ocean!"

Woman - "Maybe. But the bigger the boat, the smoother the sailing."

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Torrey Pines Sailing Team

A bunch of retards banded together to sail boats, who fight over retarded things, led by retards, funded by retards, and supported by rich retards

Did you hear about the torrey pines sailing team?
Yeah can’t remember the last time they stopped fighting and won a race

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"Well, then. We sail without him!"

Line from the movie "Wedding Crashers" uttered by the legendary Christopher Walken. Can be used whenever someone fails to show at a pre-determined time or is inexplicably missing. A more polite way of saying, "Well, if he doesn't wanna go, then fuck him!"

"Where's Sak?"
"He's still sick."
"Well, then. We sail without him!"

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hoist up the john b's sail

to say that you are going to go home

I'll see you guys later, I am going to hoist up the john b's sail.

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My ship hath/has sailed

A phrase many shippers use to say that their ship has been confirmed. Oftentimes, a headcannon.

Andrew: My ship hath/has sailed!
Mark: What ship?
Andrew: You know, my headcannon.

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A good pirate also sails on the red sea

If your girl's on her period, who cares, just fuck her.

Hey man, I want to fuck my girlfriend tonight but it's her period and it'll be a bloody mess.
- cmon dude, a good pirate also sails on the red sea.

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Sail

Slang for suicide, or a suicide attempt. Similar to the slang associated word, "off, offed, offing".

"Yeah did you hear? That guy sailed"