Xtreme singular they
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In the Metro, a free newspaper that I often pick up in Edinburgh, there is an entertainment gossip page called Guilty Pleasures, which of course I never look at. Perhaps the most poisonous of the regular features is a couple of square inches, buried amongst the candid paparazzi shots of heiresses' breasts and film stars' bellies, under the title News from the Molehill, which I certainly never look at. It has a very particular and routinized syntactic form.
The piece always begins with a wh-phrase, usually of the form which + Adjective + Noun, the noun being something like actor, celebrity, TV personality, or singer. That wh-phrase is then used as the hook on which to hang a bizarre gossip item. Further references to the unknown individual with definite noun phrases are used to supply enough clues to get you guessing as to who it might be referring to. I quote one such item below in its entirety. (They are known in journalism as "blind items", Grant Barrett tells me.) I offer it for your scrutiny not so that you can start guessing who is being talked about, but because the piece, which unusually conceals the sex as well as the identity of the unknown gossip target, uses a striking series of singular they forms. In my judgment it goes outside the bounds of ordinary Standard English: the piece is basically ungrammatical for me.
Which paranoid celebrity has become so obsessed with their portrayal in the media they are going to extreme lengths to control their perception? The increasingly reclusive singer now personally rummages through their own bins in case they've thrown out anything that would give an insight into their private life…
A which-phrase is normally an acceptable antecedent for singular they:
Which student left their laptop over here?
But in the passage about the which-phrase is a subterfuge: it pretends to introduce a sort of quiz question, but it functions pragmatically as an existential quantifier. In other words, a direct way of saying what the first sentence actually conveys would be: There is a paranoid celebrity who has become so obsessed with their portrayal in the media… That doesn't sound too bad. Indefinite NPs are fairly good antecedents for singular they — not as good as positive or negative universally quantified NPs like everyone or nobody, but pretty good. But once we know that there is a specific person whose identity is being hinted at, a real person who has a sex, and we are actually trying to think who it might be, to have a singular singular they referring to that person sounds very strange. To me, it is ungrammatical — or at the very least, highly inadvisable in terms of style.
Just one man's judgment as a native speaker. And let me stress again that I only looked at this repellent piece of masked gossip in order to discuss the syntax with you. I don't know the identity of the unnamed singer; I have no idea who they might be.
[Update: John Burke tells me that you can see the Tony Curtis character's press agent composing a blind item on the fly in the movie The Sweet Smell of Success.]