(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) -- "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*