Frederic Malle's Iris Poudre!
I say that because I absolutely adore it and everyone who's ever smellt it on me says how nice it is. It's not 'challenging' but it is beautiful and very womanly. (And this from a lass who lives in jeans.) And I think it's something you need a bit of age behind you to be able to wear.
Since you're in the US what about a few of the CBIHatePerfume smells? They're very different and interesting, especially if your friend is literary or creative. They do sample vials from the website.
And of course there's the lovely Ava Luxe - she does great samples and the descriptions on the website are excellent, so you might well be able to choose somethign that sounds exactly like your friend. Is she a Madame X, a Film Noir or a Silk?