Like his films, Whit Stillman is slightly behind his time

"Someone said the intention of this film was Judd Apatow Meets Jane Austen, but that's just not true at all." Director Whit Stillman

No, it's not true. But that "someone" can be forgiven his mistake, because a Whit Stillman film has always been hard to pin down. His signature trilogy – Metropolitan (1990), Barcelona (1994), The Last Days of Disco (1998) – are ostensibly set in specific places at specific periods, yet each seems strangely, and wonderfully, out of time, searching for its rightful home in a bygone era. These movies are verbose comedies of manners, whose youthful characters, Ivy League post-grads, speak with the trenchant wit of a Cole Porter lyric, and whose dominant tone, a heady cocktail of privilege and disillusionment, harkens way back to the lost-generation lyricism of a Scott Fitzgerald novel. No wonder the three have been dubbed the "Doomed-Bourgeois-in-Love" saga.

It's never been a secret that the trilogy has an autobiographical strain, but to meet Whit Stillman is to quickly realize how deep that strain goes. The first impression is dramatic: At 60, he too seems remarkably out of time. The unlined face, the straight dark hair just tinged with grey at the temples, certainly those penny-loafers, all belie his age. Yet it's his voice that's the real fountain of youth – so excitable in timbre, but vulnerable too, almost needy on occasion, and painfully honest when he talks openly about his long "period of failure."

Very long. It's been 14 years between films, between Disco and his current Damsels in Distress (opening next Friday and the one that isn't Judd Apatow Meets Jane Austen), an extended hiatus when his career stalled and his marriage ended, when love was lost and the haut bourgeois he is must have felt truly doomed. What happened?

Well, before we get to the doom, let's establish the bourgeois. His credentials are impeccable. Great-grandfather Stillman: President of National City Bank and an American money-bags of the top rank. Father John Sterling Stillman: A classmate of JFK at Harvard, then a lawyer serving in the Commerce Department under Kennedy. However, his parents divorced when Whit was 13, leaving him with emotional scars but precious little else – not much of the family money trickled down.

Still, he managed to make his way to daddy's alma mater, only to find this: "Harvard was depressing when I was there in the early '70s – a very grungy, political, oppressive unhappy time. I should have been happy, I was desperate to get in, but instead I was very, very down in the dumps my first years. I'm really surprised that, in a script that tries to be so stylized and fun and light and unreal, somehow so much deeply personal stuff was dragged into it."

Yes, the script he's referring to is Damsels in Distress, which unfolds at a preppy East Coast college and features four co-eds with floral names – Violet, Rose, Heather, Lily – who devote their perfumed energy to running a "Suicide Prevention Centre." This movie is quite forcefully yanked out of time. "It's set in a stylized, idealized, comic-land," he says. "The girls are retro, living in some vague past, and the film lives in the same past." So, still not a cellphone in sight, nor a Tweet to be heard in a Stillman picture. But lots of clever dialogue again, where the subject of depression, that "deeply personal stuff," gets the comedic treatment, double-dosed with an odd combo of broad farce and clever satire.

And yet, even odder, these unreal girls are also rooted in Stillman's actual past: "I went back to Harvard for a visit several years after graduating and heard about this group of girls who wore perfume and retro clothes and gave these great parties. Everything seemed different and so much more fun." The memory stayed with him and, later, inspired the screenplay. Much later. Stillman is a notoriously slow writer, although now a more confident one: "The strange thing about my period of failure, of not making a film, is that I felt much better about the thing I most worried about – writing a script. Because I really didn't feel I was best suited to being a writer. There's so much fighting with it. Now I just think people must be bad writers if they love it.

"However, when I'm actually making a film, there are always naysayers in the process and production ends up being like 18 months of pure, sweating tension. So I want to be on a film to escape the solitary writer's life, but now the solitary writer's life seems very appealing to me. You know, after Krzysztof Kieslowski made Three Colours, they asked him what he wanted to do, and he said he just wanted to sit in a dark room and smoke. I'm not a smoker, but that just seems to me the perfect image."

Which brings us back to that prolonged hiatus – nearly a half-decade of getting better at writing scripts because not a single one got filmed. The hyphen in writer-director had become a wall. Once more, what happened? Turns out life happened, but in ways that only a precariously independent filmmaker could live it. The vocal timbre gets dialled to excitable as he revs up his run-on answer: "Part of the problem was geography, not being in my homeland. I lost my apartment in New York the weekend Disco came out, I had a family with two daughters and my European wife wanted to be in Paris, although our marriage was sort of falling apart then. I lived in Paris for nine years. We split up in 2002, and then I was deeply involved with a French woman, so I got to know France really well.

"Anyway, I thought I could go to London and set up films there. I could get script commissions but I couldn't ever get the financing, because I was trying to do material that was very different – a drama set in Jamaica, and another in China during the Cultural Revolution. I turned in the script for that one on Sept. 12, 2001, which was not very opportune. Eventually, I went back to Castle Rock, who produced my previous work, with the Damsels idea. For me, this movie's different but also the same, so I'm a little worried that I've trapped myself.

"You know, it's kind of pathetic that, having made films that were generally well-received and, with the exception of Disco, profitable, there's only one person who's ever backed my movies: Martin Shafer at Castle Rock. There's only one guy who has ever said 'Yes.'"

You can hear it, can't you? That youthful vulnerability in the voice, that neediness. And with good reason. Sixty years of living, only four films to his credit, just one guy in his corner, and a comic sensibility that, in the age of Twitter, owes infinitely more to Jane Austen than Judd Apatow. So his next step seems inevitable: "I hope to settle in the Sierra Nevadas, out of an urban area, in a writing retreat somewhere." Perhaps a dark room, with a pen mandatory and smoking optional.