Whit Stillman on the set of "Damsels in Distress"
Sony Pictures Classics Whit Stillman on the set of "Damsels in Distress"

After a 14-year absence from feature filmmaking, Whit Stillman -- the beloved chronicler of preppy, privileged and highly literate youth -- makes his comeback this Friday with the release of "Damsels in Distress."

Despite his time away from the big screen, Stillman hasn't been resting on his laurels. He tried (and failed) to get a number projects off the ground, including an adaptation of Christopher Buckley's political satire "Little Green Men" and "Dancing Mood," a period piece about the Kingston, Jamaica church music scene (he told Indiewire he still hopes to get that last one made). In addition, he also penned the novel "The Last Days of Disco, with Cocktails at Petrossian," based on his last film to hit theaters, "The Last Days of Disco."

Those familiar with Stillman's brand of wordy quirk and knack for doing wonders with ensemble casts will no doubt respond well to "Damsels." The film finds Stillman in familiar territory, exploring the dynamic between a group of verbose and driven female students at an East Coast college, with whimsical glee.

Indie darling Greta Gerwig ("Greenberg") stars as Violet, the leader of the pack, who heads a group at college that seeks to help severely depressed students with a program of good hygiene and upbeat musical dance numbers. Analeigh Tipton ("Crazy Stupid Love") plays transfer student Lily, a doe-eyed beauty whom Violet welcomes into their brood.

Stillman sat down with Indiewire in New York to talk "Damsels" and how a tale about women in their early 20's actually hits close to home.

First things first: Welcome back!

Thanks a lot.

What's going through your head right now? The film comes out this Friday after a lot of tinkering on your part following its world premiere at Venice last year.

Even today I was looking at the HD transfer. I mean, it's been a fairly great couple of weeks/days. We're still waiting for the daily reviews. I think the film will have an audience. From an audience point of view, the reception seems to be positive.

Violet is quite the creation. From the outset, Lily appears to be the heroine of "Damsels," but once Violet goes through some heartbreak she comes out as the film's MVP.

I always thought that people would think she's a protagonist and like her from the beginning, because I liked her from the beginning. But then I realized, as I was working on the film and showing it to people, that we had a more complex journey to take on the film, a more complex route to the end. Part of it was that people are sort of conditioned -- with characters like Violet and her posse -- to have their hackles raised because they've seen "Mean Girls."

Also, I meant to have the Lily character very pretty in a sexy, sexy way, but not very likable. Analeigh has likeability and a naturalness that makes Lily that much more compelling. So that created a problem.  

Were films like "Mean Girls" and "Clueless" in your head while making this?

This is much more "Rushmore" I think. I didn't think about that until I was done. The easy thing would have been "Clueless" and "Mean Girls," but I think that's a false lead. And "Rushmore" is also much better in comparison.

Whit Stillman's "Damsels in Distress"
Sony Pictures Classics Whit Stillman's "Damsels in Distress"
Even though 14 years have gone by since your last film, your latest is still about folks in their early 20's. What is it about youth that keeps you coming back?

A lot of it is happenstance. I just had the idea of doing "Metropolitan" because I was in my thirties and I was looking back and I find it easier to write about a past period when I have hazy memories of the time and can reinvent it in fiction. Then I went to the next phase of life and I got "Barcelona," and then I wanted to do something about girls in disco techs.

We were kind of criticized for "Disco" and "Barcelona" because the characters were kind of young, callow and philosophizing. It's okay when they're [the age of the characters in] "Metropolitan," but as the characters got older, it's different.

[With "Damsels"] I had an idea about these girls, and I'd heard some stories about groups on college campuses who are able to change the atmosphere. So I was getting back on home turf of that crossroads period of identity formation, and I was very depressed during part of my university experience, but then I overcame that, and I felt that my personality and talents came out of that crucible.

I do have two other films I hope to do that don't have much to do with that age group. I think 16-30 is a very interesting period. If you're doing more dramatic films, it makes sense, but generally at college age, you're making your pre-life choices. Theoretically, in the old days, people used to get engaged and married right out of college. That doesn't happen much anymore. But I still meet people who meet at that age and stay together.