Interview: Playwright Preston Max Allen Is Creating a Safe Space for the Trans Community With Caroline

For playwright Preston Max Allen, the beautiful new off-Broadway drama Caroline began its life as the response to a looming deadline. Quickly in the process, though, it obviously became something more, as Allen—known for his cheerleader slasher musical We Are the Tigers—began exploring identity, parenthood, and acceptance to tell the story of three generations of women who reunite under fraught circumstances.

Caroline (River Lipe-Smith), a preternaturally bright preteen, has begun to live publicly as a girl. She and her mother, recovering addict Maddie (Chloé Grace Moretz), are on the road to visit Maddie’s estranged mother Rhea (Amy Landecker), to ask for help after they escape an abusive household. Of all the confrontations that Rhea and Maddie have during the course of the play, the one thing that isn’t a point of contention is Caroline’s identity.

Here, Allen discusses the play’s origin, the extraordinary young actor bringing its title role to life, and what it means to tell a story like this at a moment when trans visibility is an act of bravery.

This conversation has been condensed and edited for clarity.

This is a silly question because I probably know the answer, but what was the impetus to write Caroline?
I have a graceless answer: I was in Ars Nova’s Play Group at the time, and I had a deadline coming up. [Laughs] So, I was keeping track of needing to come up with something. At the same time, I was interested in writing a character who was closer to my age. I’d written a lot of high school characters, especially coming off my show We Are the Tigers.

Through all of this, I was preparing for and then having a medical procedure that means I can’t have biological children, a procedure that I wanted and was necessary for me and something I’m so at peace with. This play, consciously or not, was a lot about exploring a different parental experience than the one I’m personally going to have. A lot of my writing explores the diverging paths that my life didn’t take.

It must be a fascinating experience for you to have this play up now.
It’s definitely a fascinating time, and, I think, an effective time to be sharing this story. But kind of a nerve-wracking one. While sharing this story right now is super important, our safety has always been the most important thing to me. I started writing it in 2021, and I’ve had to make changes every year based on how much more upsetting things have been.

It feels genuinely brave for this child actor, River Lipe-Smith, and their family, to put themselves in the spotlight like this, with all that’s going on.
We were very, very lucky to have found River. When I was writing this play initially, there was always the concern of how we were going to find the right kid. I knew they were out there. The closer we got to the election and then, of course, the outcome, added a whole extra layer of “People are not going to want their kids to be visible,” or they can’t have their kids be visible. We’ve been in touch with River’s parents about safety and comfort, and that’s always been top of mind.

Were you afraid that there were going to be safety issues?
Oh, very much so. It’s not the storytelling. I’m not afraid of sharing stories that are risky in terms of representation or politics. But this is a show about a child, with a child in the cast. It’s a very—unfortunately and incorrectly—controversial topic. That was the big deal to me. When I’m writing it in my house, it’s the insular three-person world that it is. In sharing it, it’s real people, with real danger that’s actually present for all of the trans and non-binary people in the space. That’s when the real life of it all comes into the theater with us. That’s the major thing that makes me nervous.

River’s really been fabulous. They’re the chilliest kid. They’re so fun. They’re so smart and thoughtful. At the same time, they’re very much a kid. They’re playing video games. I’m the one in the background who’s terrified about the political world, and they’re doing their 11-year-old thing, which is great. I hope every kid is getting the chance to have that and not be affected by all that is surrounding them.

In an age where so many of the queer stories that are being told are still queer tragedies, Caroline isn’t one. It’s not even necessarily about being trans. It just happens to be a fact of the character’s life, which the characters accept without question.
I want people to come into the space and experience, for the length of the show, that there’s nothing weird or abnormal about being trans. There’s nothing different about this kid from any other kid. There’s nothing different about what they want or how they see themselves. That’s the goal, and I think that’s been the experience that a lot of people have been having. I’ve heard a lot of people say that it’s great to see a kid who just happens to be trans existing peacefully within their identity. I’ve been really happy that that’s been the takeaway.