I can always sense when people flirt for that personal sense of validation and it pisses me off when -
1) It is a poorly disguised cry for attention in which case I find it distasteful
2) They insult my intelligence by thinking I can't tell what they are doing
3) I am not feeling like a whore who hands out ego strokes for the flash of a cheap smile. You gotta buy me dinner first, at least
Sometimes the harder people try to flirt with me, the more I ignore them and you can see them ratcheting up 'the charm'.
Having said all that, sometimes I will play along as part of the social contract if
1) The attention whoring flirt is exceptionally smooth
2) " is exceptionally attractive
3) We have chemistry and it's fun to play around like this, knowing it is playing around and nothing more
I understand there is a fine line sometimes between flirting and socializing, but it is very rare that you will mistake me for openly flirting with you unless I actually am. And I will RARELY openly flirt except for in certain 'green light all go' situations such as a club or bar where its a hotbed of singles' activity.
There is something intensely distasteful to me that people would use sex/sexuality/promise of sex/romance etc. as a lure for attention. People who try to seem intelligent and turn into grammar nazis or some other kind of contrarian know it all pisses me off, but it's such an OBVIOUS shtick I guess it's easier to wave away. I think partly what bothers me is that flirting is often very lazy. Also, there is certainly a kind of flirting that is basically smugness - i.e. "I am so hot/attractive that obviously you must want me, because if you haven't noticed, I'm much hotter than you and you should consider yourself lucky that I'm talking to you". Maybe I got screwed up in the head somewhere growing up, because that is exactly how I interpret a bulk of flirting by strangers, especially people who are trying to sell you something more or less.
Having said all that, even if you do it poorly, if you are trying to be charming (or, as some would say, they just "are" charming ) or entertaining or witty or flirty, go for it. Go for the gusto if that's how you do. But, please try to be GOOD at it, otherwise you get the polite ENFP pokerface or my best impression of a bored INTP (and it ain't pretty).
Also, I distinguish the kind of flirting and intent described in the thread with flirting in general and especially with joshing around with friends or people you have basically given permission to play around with you. I dunno, people's definition of 'flirting' is so wide, sometimes it includes what I consider innocuous or good-natured and platonic playing. So I'm addressing a very narrow definition of chronic flirting (?) as described in the the OP.
Wait - I just realized --
To sum it up, being an SO primary I am VERY aware of power plays and social dynamics. When people very baldly flirt with me for an ego stroke or to coerce me into doing something, I honestly do feel insulted and almost like my social self is being pawed inappropriatedly by an overly eager puppy. My instinctual response is 'Get the fuck away from me'. But, I'm way too socially aware and polite to say this so I do the next best thing, which is the robot stare.
BTW, if this is the second or third time I've posted in this thread, disregard everything except for this latest post :P