Pussy Sailing

a term that means looking for girls/pussies.
looking for wiling girls to have sex.

"Man, It's been a rough week."
"Yes, we should go pussy sailing."
"Indeed"

by De Jay Hemmingston January 18, 2010

smilin Jack

A condition that occurs when one is shooting a semi-automatic pistol and runs out of amunition. The slide locks back in the open position. This is especially troubling in the middle of a gun fight because your opponent now knows your weapon is empty.

Paul was in trouble, he was surrounded and his piece was in smilin Jack, he might as well been holding his dick in his hand.

by Jackel in Brawley April 13, 2007

Sailing on the Pumpkin Tide

Refers to becoming drunk while alone in order to enhance one's creative process. Probably originated in the webcomic Problem Slueth.

Person 1: Can you come over tonight?
Person 2: No, I've had some ideas rolling around so tonight is going to be for sailing on the pumpkin tide.

by Analog_man June 18, 2011

Siling

A kind person with an even kinder smile.

She's a real Siling!

by rocketleaguenerd01 May 8, 2022

Both lips smiling

A phrase from Tiktok “both lips smiling” her face and 😸 lips smiling 😨🙏🏽

“You got both lips smiling right now 😇🙏🏽”

“Girl he’s so fine he got both my lips smiling 😜😍”

by Meli 🩷 July 27, 2023

sailing

A sport that includes leaping over centerboard housing every time you tack causing lots of bruises and cuts on your legs; especially in a 420 (by the way - it's a type of boat - nothing to do with pot dumbasses) and if you are lucky enough not to be cut or bruised on your legs you probably have a concussion from being too slow to duck during a tack or gybe.

Sailing is the best sport EVERRR

by Sailor_Savvy September 3, 2007

Sailing mishap

Accident involving a sailing yacht.

"You look the same age to me."
"I'M FIVE YEARS OLDER AND IN COLLEGE!!!"
SAILING MISHAP!!!!

by Snake January 16, 2005