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Demonic Gentleman 

A Demonic Gentleman, is a man that is considered by other to be weak because they are usually take the high road, very few things makes a Demonic Gentleman gut up to fight, but when they do fight? They fight like hell.
Guy 1: Hey man just leave Jason be.

Guy 2: Him? He's just a pushover.

Guy 1: Nah man, he's one of those "Demonic Gentleman" types.

original gentleman 

Original Gentlemen is the new OG. An Original Gentleman is a Renaissance Man. The “OG” has been replaced by the Original Gentleman (OG). He is very respectful of everyone and always willing to extend a hand to help anyone in need. He’s a Lover of Life and Al, that it presents.
Frank is a wonderful person, must be an Original Gentleman (OG). He is always smiling and respectful of others.

The Gentleman's Disease 

A more elegant way of saying autism
My Doctor just told me I had the Gentleman's Disease

the gentleman's surprise 

Urban Dictionary-
The Herman, also known as, The Gentleman's Surprise.
To preform the Herman, ejaculate in an object that is commonly used by someone unbeknownst by the owner or frequent user of said object to leave a nice surprise. Such objects can be, but are not limited to, shoes, helmets, pockets, socks, hats, opened alcoholic drinks, and even wallets and purses, preferably while they are not in use.
"herman left the gentleman's surprise in my brother's helmat, hah hahhahahahahaha"

southern gentleman 

A man who goes down for cunnilingus on a woman first. Thus he "goes south" to ensure the woman orgasms first. As a gentleman should.
Girl: he was a total southern gentleman. I came twice then he sung me "ring of fire."

Supreme Gentleman 

A sign of respect when a man ejaculates into a top hat and places it on another man's head.
My dentist gave me a supreme gentleman and we've been great friends ever since.
Supreme Gentleman by twitter_bot October 1, 2020