Joe: "You know Sly and Kawola?"
Jane: "Umm, no. who are they?"
Joe: "Well,you should they are two the dopest rappers comming out of the midwest!"
Jane: "Umm, no. who are they?"
Joe: "Well,you should they are two the dopest rappers comming out of the midwest!"
by EyeNoHiphop January 2, 2012

Showing in an insinuating smile that shows to have some secret knowledge that may be harmful or embarrassing to the person the grin is aimed at.
by JustMae November 2, 2013

by Kieran1991 February 22, 2009

It is a British term. It can be used as a player but is Normally used as a name for a man trying or making the first move such as, holding hands, a hug, or, a kiss
by Jenna Axe November 2, 2016

Multi-purpose phrase used to describe something either good or bad. Context is based upon tone of voice or tone of conversation.
Use in positive context;
Matt; "I can't 'effing wait to go on holiday!"
Mike; "Yeah man, it is going to be so pro-sly!"
Use in a negative context;
Lloyd; I just crashed your car mate"
Dave; "Not cool man, very pro-sly"
Matt; "I can't 'effing wait to go on holiday!"
Mike; "Yeah man, it is going to be so pro-sly!"
Use in a negative context;
Lloyd; I just crashed your car mate"
Dave; "Not cool man, very pro-sly"
by PuffingTheHerb July 19, 2011

A sly five is essentially a high five, but can only be used appropriatly when somebody has accomplished something very sly.
Two kids at school steal a friends pencil case with out him noticing.
Kid 1#:wow, your really sly at stealing things
Kid 2#:this calls for a sly five
Two assassins kill their target from one thousand feet away using a silenced sniper rifle. Nobody notices.
Assassin 1#: omfg that was awesome
Assassin 2#: sly five me
Kid 1#:wow, your really sly at stealing things
Kid 2#:this calls for a sly five
Two assassins kill their target from one thousand feet away using a silenced sniper rifle. Nobody notices.
Assassin 1#: omfg that was awesome
Assassin 2#: sly five me
by jedimasterjames January 15, 2010

purposely talking about someone who's friends with you on facebook or follows you on twitter/instagram/tumblr.
friend one: yo, did you see that she was sly diggin' her ex on twitter
friend two: yeah, i really don't why she's still doing that. it's been a year after their break up
friend two: yeah, i really don't why she's still doing that. it's been a year after their break up
by Amelia Bottomly January 8, 2013
