(1) -- A shady male character who has a decieving smile, à le chat Cheshire.
(2) -- A questionable song that sounds charming but at the same time, seems to have darker meaning.
(3a) -- An uber-slick gentleman with a too-enthusiastic smile. Often the gent is hyper-sexual, or enjoys violence.
(3b) -- A Cheshire dandy can also be known by other names, as long as Cheshire accompanies the insult/phrase used.
(4a) -- Old-timey charm mixed with provocative intent.
(4b) -- Cheshire can also be used on its own to speak of a gent.
(2) -- A questionable song that sounds charming but at the same time, seems to have darker meaning.
(3a) -- An uber-slick gentleman with a too-enthusiastic smile. Often the gent is hyper-sexual, or enjoys violence.
(3b) -- A Cheshire dandy can also be known by other names, as long as Cheshire accompanies the insult/phrase used.
(4a) -- Old-timey charm mixed with provocative intent.
(4b) -- Cheshire can also be used on its own to speak of a gent.
(1) -- I want to say I believe James' smile, but he seems awfully like a Cheshire dandy.
(2) -- "Where we dwelt by the river, sipping on tea from Long Island, and playing where's the ribbon...? What marvelous times we had, I with my fingers dipped oh-so-sweetly in that cherry pie of yours, dove."
People: "Man, did you hear that song?? What a Cheshire dandy, eh?"
(3) -- "Hey sweetling, want to blow this popsicle stand and head back to my McMansion? I've got a leather collar with your name written ALL over it! Then after, we can watch Boondock Saints. You know how I love watching all the fighting. It gets me so effin' hard. You like it rough, don't you baby?" (insert slimy git grin here!)
Girl: No thank you, damn Cheshire wanker. You're really starting to creep me out.
(4) -- (a couple approaches the stairs)
Guy: You first, sweetling.
Girl: Alright. *starts walking up*
Guy: *behind her* (insert Cheshire grin here!) Damn that ass is hot. Wonder if she'd let me bend her over right here....
Girl: What did you say?!
Guy: I mean, baby, you are the essence of my very soul! Do you know how much I adore you?
Girl: You're such a Cheshire. I KNOW you were checking out my bum.
Guy: *caught red-handed*
(2) -- "Where we dwelt by the river, sipping on tea from Long Island, and playing where's the ribbon...? What marvelous times we had, I with my fingers dipped oh-so-sweetly in that cherry pie of yours, dove."
People: "Man, did you hear that song?? What a Cheshire dandy, eh?"
(3) -- "Hey sweetling, want to blow this popsicle stand and head back to my McMansion? I've got a leather collar with your name written ALL over it! Then after, we can watch Boondock Saints. You know how I love watching all the fighting. It gets me so effin' hard. You like it rough, don't you baby?" (insert slimy git grin here!)
Girl: No thank you, damn Cheshire wanker. You're really starting to creep me out.
(4) -- (a couple approaches the stairs)
Guy: You first, sweetling.
Girl: Alright. *starts walking up*
Guy: *behind her* (insert Cheshire grin here!) Damn that ass is hot. Wonder if she'd let me bend her over right here....
Girl: What did you say?!
Guy: I mean, baby, you are the essence of my very soul! Do you know how much I adore you?
Girl: You're such a Cheshire. I KNOW you were checking out my bum.
Guy: *caught red-handed*
by Experimental Mistress October 13, 2009
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Cheshire cop:"hey look a nigger"!
Nigger:"oh shit better run!"
Cheshire cop:"tag and bag that nigger!"
Nigger:"oh shit better run!"
Cheshire cop:"tag and bag that nigger!"
by BigCCCC February 1, 2014
Get the cheshire cop mug.A school full of people who think they're the shit; CHS has girls with big titties and some flat chesters too. But no matter how good you look, as a girl, you must wear clothes that make men's lightsabers enable. They all think they live in a schetchy area because a kid got arrested for selling drugs once. They like to show off their wealth by wearing expensive clothes and having more expensive cars than your mom or dad.
CHS kid: I got a gucci belt bro!
Wallingford kid: I got food today!
Wallingford parent: Those Cheshire High School fags
Wallingford kid: I got food today!
Wallingford parent: Those Cheshire High School fags
by Niggaraguacamole September 27, 2018
Get the Cheshire High School mug.A really rich town in Connecticut that belongs in fairfield county. Everyone's parents are either CEOs or VPs. All the guys wear polos from lacoste or ralph lauren and all the girls have lots of accessories from chanelle, prada, dolce gabbana, and coach and loads of jewlery from Tiffany and Cartier. Nobody knows what a knockoff or a sale is and most of the houses price well into the millions. Everybody owns at least 3 luxury cars. Everybody spends their summers in Cape Cod, Nantucket or at a snobby Country Club where they play golf and tennis. And everybody is white.
by J. J. Smith December 25, 2007
Get the Cheshire mug.Cheshire is a county in the north west of England. It's mostly posh and pretty rich, filled with people too proud to say they're from the North.
The more affluent also love to look down on the lesser areas such as (the admittedly shit) Ellesmere port.
The more affluent also love to look down on the lesser areas such as (the admittedly shit) Ellesmere port.
by Luke2002 May 31, 2020
Get the CHESHIRE mug.by M4_Cruiser August 8, 2020
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