gentlemen never sail to windward

"nice-guys don't go for anal"

Chantal: I thought gentlemen never sail to windward.
Rodriguez: I'm no gentleman, baby.

by Carl Figleaf August 14, 2022

gentlemen

A sexy ass man

Mother: Is that a gentlemen
You: no that's a penis

by Ashley Foti's balls October 28, 2022

Gentlemen’s Woman

A lady who gets all the guys. The female version of a ladie’s man.

“I’ve never seen any gentlemen’s women portrayed in media ever. I thought I’d see some?” -me

“Erica the gentlemen’s woman gets so much dick she’s living the life” -Stacy

by Superjuliam November 22, 2022

Gentlemen's purse

A scrotum

Please do not kick me in my gentlemen's purse.

by anonymous December 14, 2023

Gentlemen's Ambition

The instinctual human desire to immediately drink another ice cold beer upon completion of an ice cold beer.

"It is very difficult to control my gentlemen's ambition."

"My wife hates my gentlemen's ambition."

"Concealing my gentlemen's ambition becomes more difficult and tiresome each passing day."

"Nothing better than indulging in a little gentlemen's ambition alone in my garage while listening to my favorite Daughtry album."

by Ambitious Gentleman March 15, 2024

gentlement

a man who is gentle and meant what he said

What gentlement really came through today.

by mebc June 27, 2024

gentlemen of culture

this is how dudes commenting on thirst trap (and often ai-generated) youtube/facebook/tiktok videos salute and acknowledge each other's motives and aspirations

"Gentlemen of culture, we meet again>"

by nouiknouik May 3, 2025