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

Gentleman's Crush

When an older guy lusts after some person considerably younger and immature, realizing he won't/can't proceed with intimacy/sex because she's just too out of touch with the values and tastes He enjoys.

Hey, Man. You think Pops is gonna hook up with that chick that's swooning and drooling like he's a Tater Tot???

"No, Dude. He told me he's got a Gentleman's Crush on her, and put her off limits. Now they're just friends, but She may not get it..."

by MeO'MyOh! August 24, 2022

Gentlecuck

The guy who loses the girl he likes because, according to him, he is being respectful/a gentleman but in reality is afraid of taking the next step.
The girl gets stolen away by a guy who is not afraid to move things forward.

AKA the initial romantic interest in a NTR.

A: "After all this time, I really though him and her were gonna end up together."
B: "It was never gonna happen. He's too much of a gentlecuck."

by SVG9 August 28, 2022

Gentleman’s Hotdog

Where a couple hotdogs but the man is overly polite and checks in for consent several times

Remember when you gave me that gentleman’s hotdog?

by MartyMayhem September 9, 2022

Gentleman’s Inch

When you have a girlfriend but someone’s taking a group pic and you have to put your arm around another girl, so you hover your hand an inch away from her body.

Guy 1:“Bro, what’s your girlfriend gonna think about your arm around Trinity in this picture!?”

Guy 2: “Relax bro I made sure to keep a gentleman’s inch”

by Lindsey Wong September 16, 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

guttlebus

A bus where within your homie suckle your shmeat until you are coated with jizz along with your homies the males inside the bus are not gay they are simply homiesexual.

Jackson: last night's bus ride home from the game was straight up a guttlebus
Bryce: No cap I guttled at least 30 oz of your semon alone

by Guttlebus November 7, 2022