At twenty-seven, Alison Pill has already had a marvelous career. She has worked with Woody Allen twice (first as Zelda Fitzgerald in Midnight in Paris); appeared in Gus Van Sant’s Milk (as the lesbian activist Anne Kronenberg); starred in the Broadway revival of The Miracle Worker as Annie Sullivan (reviving a role originated by Anne Bancroft); received a Tony nomination for her Broadway debut in The Lieutenant of Inishmore; was a regular in the HBO therapy drama In Treatment; and stars in the Aaron Sorkin drama The Newsroom, playing the neophyte reporter Maggie Jordan. The New York Times called her performance in Neil LaBute’s play Reasons to Be Pretty “commandingly intense and authentic,” which she always is. And she has worked with a spate of interesting and seasoned actors: Sean Penn, Jeff Daniels, Sissy Spacek, Steve Carell, and Gabriel Byrne.

Born and raised in Toronto, she spent some years in New York doing theater, and now spends part of the year in L.A., where The Newsroom is shot. Her home, however, is in Montreal, with her fiancé, the writer and actor Jay Baruchel (perhaps best known for his role as one of the stoner friends in Knocked Up).

Whenever I told anyone that I was interviewing Alison Pill, after a moment they would identify her as the girl with the “round face” or the “moon face”: a feature that’s kind of hard to miss. Her pale, wide-open face and round, wide eyes are absolutely distinctive—giving the promise of total transparency—which would not be so interesting if it wasn’t balanced by her remarkable self-possession, suggesting that the illusion of access cannot entirely be trusted.

We met at a Vietnamese restaurant in Toronto last August, while she was in town visiting her family. After lunch, we sat in my garden. She was playful, enthusiastic, and sharply funny and smart. She made silly voices, mocked herself, and laughed after most of what she said in a high-pitched and giddy way.

We spoke about her desire to have “kiddles,” and she talked about her early heartbreak at being kicked out of Claude Watson, the beloved arts school she attended as a child; they complained that she was missing too many days (she has been working professionally since the age of eleven). Still upset over it, she recalled them telling her, “You are a waste of space.” Yet among a crop of young actresses who are constantly being pumped out—here one season, gone the next—Alison Pill is anything but.

—Sheila Heti

I. “HE’S LITERALLY, LIKE, HOLDING ME”

THE BELIEVER: I really wanted to be an...