1) While nobody in his or her right mind would characterize Whit Stillman as a "realist" or a maker of realistic films, I would still insist, allowing for the limitations of my particular perspective, that his 1990 debut film Metropolitan is a scrupulously accurate and, yes, even realistic portrayal of both the social class it depicts and the people within it. One reason that people tend to resent what they refer to as "elites" is indeed because those entities are pretty much closed circles. And the conditions within those circles are quite strictly circumscribed. Allow me to offer a supporting anecdote. Stop me if you've heard this one before, or skip ahead, because I'm not actually going to stop. A friend of mine used to play bass in a band led by a singer-songwriter who as it happened was a child of social/financial privilege. Her world was Jewish, not White Anglo Saxon Protestant, but that aside, the bubble effect was largely identical to the one enjoyed by the characters in the Stillman film. In any event, one day, after a rehearsal (I place this anecdote some time in the '70s), the singer-songwriter asked my friend what he'd be up to, and he told her he'd be taking the subway downtown to meet a friend, and the woman, who by this time was at least in her early thirties, got very excited and asked my friend if he would show her his subway token. Because she had never seen one in anything but a photograph before.
And every time I watch Metropolitan, I think of a cousin of mine and how he showed up at a family one Christmas, swaining with a group of buddies from school shortly before he flunked out (or something) of Columbia. My uncle never aspired to WASPdom, but there were periods wherein a kid or two of his did (this relative was and remains a Brooklyn Heights pioneers), usually with hilarious results. Anyway, this was the late '70s, and he and his buddies showed up in rather ill-fitting evening wear and insisted on drinking from standard 4.5 ounce cocktail glasses, where the hell they got them from I'll never know, and they clearly got off on swaining around as if they were in a Wodehouse novel or something, and yet there was a slight ersatz quality to the enterprise. Except for my cousin's group's ringleader of the unknotted bow tie, who was somehow clearly the real deal and was soon to regret having allowed some of his lowers to adopt his costume, as it were. Very strange.
So yes: I'd say that Metropolitan offers an entirely credible and acute look into a real world that the likes of you and I have such limited access to that, yes, given its inside-the-bubble perspective it might as well be science-fiction.
2) Stillman's subsequent and unfortunately infrequently-produced pictures have the same bubble in common. Barcelona's theme and storyline concern how the inhabitants of that bubble behave when the bubble is somehow pierced. The Last Days of Disco, among a great many other things, looks at the decline of both an actual real-world cultural phenomenon that in the film is also a stand in for One's Youth, and in its light but poignant way concerns itself also with the taking on of "responsibility," both in the quotidian "adult" sense of looking after yourself but also in a larger, moral sense. But the rarefied atmospheres of those films and the extremely precise and idiosyncratic dialogue spoken by their characters would not fully prepare a viewer for the strangeness of Stillman's new Damsels In Distress, which I would characterize as a full-on fantasia.
But not an unserious, not to say frivolous, fantasia. I understand the film's lead character, Violet, played beautifully by Greta Gerwig, seen above, as both a Stillman spokesperson and self-criticism, and I mean that entirely in an intellectual sense—I don't believe this film is any type of confessional in the conventional sense. Let us take just one example of the Violet view of the world/life. When Violet talks about finding the scent of a bar of motel courtesy soap to be "transformative," yes, it's funny, but it's not entirely a joke. Personal hygiene as a touchstone of not just physical and mental health but also of moral order—I think this is an idea that Stillman takes very seriously indeed. But he is also acutely aware as to how peculiar this idea at first appears in the "real" world that's outside the movie, and how Violet's championing of this makes her seem a little ridiculous. The whole scheme of the movie's whimsy rests on this tension, which is why the delivery of the dialogue in this picture is by necessity a trifle more formal and declamatory than it was in Stillman's prior films, which, you know, have LOTS of dialogue. (There's more than a slight touch of Mamet here, in the way the actors, even the ones playing rather absurdly stupid characters, make sure the attentive viewer will feel every comma.) The way the character played by Adam Brody descibes how in his view "decadence" has ruined homosexuality is offensive on the face of it, but the argument behind it, that a thing cultivates a more legitimate/authentic/coherent aesthetic/moral coherence by virtue of being suppressed or needing to be kept secret is, I think, something that Stillman feels rather deeply, and this film's form is necessarily an articulation of the collision of his unusual ideas and the place that he's trying to pitch them.
3) Throughout the film, I was thinking, "This kind of reminds me of a Rohmer picture," but not of the ones the French writer/director is best-known for, and I couldn't put my finger on it, and this morning I did. It's 1993's The Tree, the Mayor and the Mediatheque, one of his most obscure (it never received proper U.S. distribution and is dauntingly difficult to see here). Thinking on it now, I wouldn't be a bit surprised if Stillman knew the picture well, so pronounced are both the thematic and modal similarities. Rohmer's film posits eccentric notions culled from a classically conservative philosophy; its characters speak not just formal dialogue but sometimes actual verse; and the film ends, like Damsels, with a relatively full-blown musical number. Some enterprising programmer should try to book a double feature of the two films one day. Seriously.
4) The peculiarity of Damsels has led some people who would very much like to posit themselves as stalwart Stillman people to evince some disappointment. This is particularly exacerbated by the fact that—because Stillman writes such "strong" female characters, and because Greta Gerwig is Greta Gerwig—Gerwig or Stillman or some some weird combination of Gerwig and Stillman seem to have been appointed at this cultural moment (and in some circles) as the Vice President(s) of Feminism,the new media's sassy-and-smart division, or whatever (Lena Dunham is the current president, not that she really asked for the position). This being the case, the actual, unclassifiable-by-dogma work produced by these individuals is seen not just as weirdly wanting, but as also LETTING DOWN Our (their) Side. I won't cite, or link; you can find the suspects, as they're not too unusual. Instead, I will (again) quote Robert Christgau, from his 1975 review of the Robert Fripp/Brian Eno masterpiece No Pussyfooting: "Although art-rockers praise Fripp's undulating phased guitar and Eno's mood-enhancing synthesizer drones, they also complain that it all gets a little, well, monotonous after a while. That's the problem with art-rockers—they don't know much about art."