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Gentleman's Challenge 

A competition in which multiple teams of 3 members each compete to see which team can consume a 30 pack of beer, 3 grams of marijuana and a sheet pizza first. This competition is so called because after about an hour after the competition has begun, all teams are so high, drunk and full of pizza that nobody cares about who wins and just end up enjoying each others' company. As gentlemen (and gentlewomen) do.
Philip: "I must say, William. The participants of this year's Gentleman's Challenge are really in the spirit of the competition."

William: "Indeed, sir. It appears no one has given a single fuck about winning since the third blunt was rolled."

Gentleman's completion

For a man to bring himself to an an honourable and satisfying climax through masturbation.

Sit back, relax, and bring yourself to a Gentleman's Completion
"Bloody hell, have you seen those pics of Jessica Simpson? I had to go home in a rush..."
"How was it?"
"Gentleman's completion..."

Gentleman's Cane 

a man's genitalia, his penis, his dick, his cock. a more elegant way to discuss your member like gentlemen.
"My, that chap's gentleman's cane is exquisite"
"Are you ready to receive my gentleman's cane in your mouth?"

Gentleman's Cut 

When a man shaves his genitals in such a way that the balls and shaft are entirely hairless and the pelvic region is freshly trimmed to a short length. The idea of this grooming style is to maintain a gentlemanly status when a woman gives oral, as any areas her mouth may touch will be hairless, but the non-shaved pelvic area maintains a mature look.
I went down on him last night and he had a fresh gentleman's cut. I sucked him better than any woman had ever before.
Gentleman's Cut by Karl Kaufman December 3, 2022

the gentleman's choice 

if something or someone is a little better than other options available, thus making it only fit for someone of similar quality, a true gentleman.

gentleman's chode 

A "sophisticated way" to describe a small dick or chode.
"Tom's a needledick!"
"It's not a needledick, it's a Gentleman's chode!"
gentleman's chode by Phil M'Crackin December 15, 2008