Tipton's initial attraction to Stillman's script: "It's driven by females, and it's smart, and it's layered."
Stillman plays and cheats the period: "A lot of people are confused about the period [of "Damsels"], and as well they might be. Because it's essentially these characters, more or less in a contemporary setting, trying to recreate the past and trying to live in the past. And so it should be confusing. All of my films have kind of cheated on period because it becomes kind of a prison. Once there's this sort of hermetically sealed period, done with art directors and tons of money, somehow it limits things and makes things false. Because we actually don't live in period, we live in now."
Stillman said that before production he only knew Gerwig "from a photograph" but that "the inspiration for the fashion and the style was supposed to be Grace Kelly. Greta can have a Grace Kelly air about her, and then Analeigh actually plays a real person in the film. It's sort of like 'The Purple Rose of Cairo,' where they drop Mia Farrow into this fantasy world."
Learning to speak Stillman: Tipton described being brought into the filmmaker's "fantastic" world and learning his distinct language, his "'Whit-isms'...Whit as a director is very specific. What was hardest for the actors in so many ways was the language. 'Yes.' I don't know if you count the amount of times you say 'Yes' instead of 'Yeah' during a day, but for me I say 'Yeah.' Things were so precise. Having to sit there and make them feel and sound natural, it's wonderful for actors, but it was difficult. We would add an 'Um' and he'd come out and -- "
At this point Stillman jokingly interjected: "Oh, come on. There was a lot of freedom on the shoot."
Of his distinct dialogue, Stillman said, "The script isn't very successful on set. There's tons and tons of editing. Because yes, the dialogue is prolix, but the actors help you trim it."
One thing that is not a Whit-ism? "No strong language, please."
Lena Dunham auditioned for "Damsels": Stillman's fellow New York indie read for a small part in the film. "Lena was going to play the Alia Shawkat role, the angry Mad Madge in the corridor shouting at Greta. But you realize [that a script] has no real melody until actors say it. When Lena came in, it was for one of the comic parts, and it had been an audition session where nothing sounded right, and you really get worried." But: "We became friends."
Aside from helping each other out during production, Stillman and Dunham hold similar views in terms of shooting format: "There's this sneering that goes on about shooting digitally, " says Stillman, "but I think that's misplaced."
There was a 13-year interim between Stillman's previous feature "The Last Days of Disco" and "Damsels." What was he up to? "Loafing. No, I was failing. Orwell wrote a really great book called 'Down and Out in London and Paris,' and for a while I was thinking this would be a good project to do, and then I realized I was doing down-and-out-in-London-and-
Stillman's possible future project: "It's actually a Ska Rocksteady film, pre-Reggae. So the idea would be '62 to '66. I hope it will happen someday -- if everyone recommends this film to their friends."