I was sitting at a bar and a guy came up and said, "Are you seeing anyone?" and then before I even had a chance to answer, he said, "You should call them, tell them it's over."
That's a classic cocky-funny line. You can read an insane amount on this stuff here: http://www.reddit.com/r/seduction/comments/1uidwl/the_ultimate_how_to_guide_to_cocky_funny/
There's a thin line between cocky-funny and "asshole" - and honestly that's why it usually works.
Chicks can do cocky-funny too, of course. It's an overtly sexual technique typically but that doesn't mean you can't use it to upgrade a hookup to a relationship if that's what you really want from a guy.
However, please, for the love of all that is holy, never use the Marilyn Monroe quote.
|This quote is the meme that won't die.|
Sometimes I use cocky-funny to break people's aliases as well when having counter-HUMINT fun. To do this, walk up to any Isreali "student" at a security conference and say "Which military unit are you with?" with a big smile. Basically the cocky-funny technique is that you "assume" their cover is already broken, the same way when you approach a girl at a bar you assume they already are going to sleep with you.