Q&A with Cassandra Rose: Theater and Screenplays and Games, Oh My!
Did you know it’s possible for one person to write 300 plays in just a few years? Or that there are writers who have the fascinating job of adapting romance novels into video games? As soon as I learned these things about the lovely and talented Cassandra Rose—who I met through Austin Film Festival, where she won the Scripted Digital Series Award with her script Walk Into A Bar—I knew I needed to know more about her creative life.
Originally from Rockford, Illinois, Cassandra grew up doing historical reenactment, giving tours in a science museum's coal mine, and working at a literacy nonprofit. As a playwright, she followed up a BA in Playwriting at Columbia College Chicago with a decade of Chicago playwriting self-productions and residencies, including Chicago Dramatists' Tutterow Fellowship. Then she left it all behind to move to LA and pursue screenwriting, and earned her certificate in Writing for TV from UCLA's Professional Program. She’s adapted romance novels into choose-your-own-adventure video games as a Narrative Designer for Chapters: Interactive Stories. She’s also been contracted by Wondery to write episodic audio fiction. No matter the format or genre, she writes scripts about people who make genuine connections in surprising ways.
In our interview, Cassandra generously shared her varied experiences with crafting scripts about all the things for all the formats. While obviously a hard-working writer, she delights in the creative work of each process. Ultimately, as she says below, “writing is writing.”
Q&A with Cassandra Rose, writer
Q: What do you write?
A: Basically? I write scripts. My bachelor’s degree is in playwriting, so I started with that base of knowing how to write for people in a space talking and interacting with each other. It was an easy jump from playwriting to screenwriting. Though I entered screenwriting with an eye for episodic storytelling. In playwriting, everything is always so final. So in screenwriting I found a lot of joy in getting to stick around with these characters for a longer time. With that said, what won Austin Film Festival for me—even though it’s a web series—it’s an anthology. So each episode is self-contained like a short play.
I wandered into audio drama because there were a couple theater companies in Chicago doing radio plays. Then I got serious during the pandemic when there was a radio play resurgence, and Wondery approached me to write for them. By that point, I was like, “What’s one more storytelling format?” So I branched into new media and started to adapt romance novels into a type of video game known as visual novels.
Q: So you’re doing all those things at once—playwriting, video games, and screenwriting?
A: Yeah—I like to think of it as having a balanced writing portfolio, that it kind of ebbs and flows. During the pandemic, theater mostly went away so I kind of stopped writing plays. But! A lot of theaters I knew pivoted to audio drama and web series, because they were more Covid-compliant. Same story for video games, which, in many ways, are the most Covid-compliant. I have a high-risk partner, so as theaters started coming out of lockdown, I wasn’t very eager to return to the all in-person world of traditional theater. Luckily, I have the rest of my writing portfolio to keep me busy.
Q: What are some of the differences in how you approach these mediums?
A: I take a lot of comfort in the fact that writing is writing. No matter what medium you’re in, it's always, “What’s a great story? What’s the character going through? What do I want my audience to go through via that character?” Beyond that, it’s: “What are the fun things I can do in this medium that I can’t do in another medium?” Before the pandemic, I was experimenting with theater companies on how liminal you can get—which, in film, you can’t do. It’s all concrete: you walk into the room, you see the whole room. There are books on all the shelves. The people are there. It’s very specific. But on stage, you can be looking at the stage and seeing these characters in the GLBT Historical Society Museum in San Francisco, in present day. But if this actor puts on this trench coat, suddenly we all agree it’s 1970s San Francisco and they’re in a newspaper editors meeting talking about whether they should print the story outing somebody as gay or not. Having those two things at the same time, showing off those facets—that’s what I do in theater.
In audio drama, it’s all about the sound. It’s a private medium because of how we consume it. Back in the day, the whole family would gather around the radio, but now it’s just headphones. That’s the area where I go more into thriller and horror, because there’s that terror of, “Oh god, I’m hearing something that nobody else can hear. Do I need to get help?” I also love with audio that we all intimately know the sound of hot versus cold water, we know the sound of rustling paper—you can make those pictures without having to narrate everything.
For video games, it’s all about choices. The player becomes the main character. So, it’s thinking about: What are all the variations of a person that can exist in a moment? Is the player wanting to be snarky? Heartfelt? Brave? You make those options available, so when the person’s playing it, they’re like, “Oh my gosh, this really is me in the game.”
Q: Is it a weird transition if you’re in video game writing mode—coming up with many different paths—and then you move to a medium where you just pick one story path?
A: It can be weird, yeah! But in a delightful way. With the branching narratives that are possible in video games, sometimes I feel like I’m playing three-dimensional chess with myself. I’m trying to prove to a person who may be playing on this platform for the very first time, like, “Hey, your choices actually matter. People in this game will ‘remember’ what you say and do.” It’s also about cause and effect. We don’t want to be super punishing in our games because we don’t want people to rage quit, but we do want them to feel like their choices matter so they’re engaged and invested. So, if they do a test, like, “Let me see if this narrative will course correct itself if I choose to spill a drink on the love interest,” it’s like, “No no, when you see this character again they’ll be like, ‘Oh, you’re the person who ruined my sweater.’” Those kinds of things are fun to play with.
When I get to a screenplay, it feels really delightful to have imperfect characters. In a video game I have to write it more towards you playing this, which can sometimes feel like, “You’re making great choices sweetie, we’re so proud of you!”
Q: Whereas writing a character doing bad things is not something you’re doing to your audience; your audience can distance from that.
A: Yeah, there’s a difference between us enjoying Walter White murdering his enemies, versus us playing a video game, and the game’s like, “You just murdered people and everyone hates you.” Because at least for me, when a game tells me that, I’m like, “Well, I don’t know if I want to be in this story anymore!”
Q: Specifically, you adapt romance novels to video games. What is that process like?
A: Basically, if you go into the Chapters app you’ll find interactive adaptations of published romance novels. Our adaptations tend to be about twenty chapters long. To get to that length, I’d say I have to add or build out about 50-70% more material than the original published novel had. I tend to do a lot of romcoms and friends-to-lovers stories, so they’re just filled to the gills with romance tropes and shenanigans. And each chapter you’re making, like, two dozen different choices. There’s a final moment at the end of each book, where it’s like, “Do you want to live happily ever after with this love interest, or would you rather just be friends?” And if people choose that ending, they often have weddings, have babies—there’s all this wish fulfillment.
Q: I love the idea of writing wish fulfillment for people.
A: Yes! I personally love reading fan fiction, because I love that feeling of, “If only these characters could just get their shit together and explore what’s possible…” So writing the wish fulfillment parts, or growing and deepening the relationship’s journey, is one of my favorite parts of the book-to-video-game adaptation process.
Q: Tell us about “The Dictionary Project,” when you wrote a lot of a short scripts in a short period of time.
A: A few years after I graduated from college, this opportunity came up—The Kenyon Playwrights Conference hosted by Kenyon College. It cost two thousand dollars, and I was like, “I’m in my mid-twenties, I don’t have two thousand dollars.” So, I set up a crowdfunding campaign. I said, “Hey friends, if you can give me money so I can go to this playwriting conference, my reward to you will be a short play I write for you.” I had it in three tiers. The lowest level was a one-page play. Mid-range was a three-page play, but they had more control over the story so they got to choose a dramatic element—like, one person asked me to write a three-page play that had Nikola Tesla in it, another person wanted the color aquamarine to be there. And then the top tier was a ten-minute play. It not only had a dramatic element, but it also had a genre. The person got to choose if I had to write a sci-fi, a fantasy—I also had people who were like, “Write in the style of Anton Chekhov,” “Write in the style of David Mamet.”
And I was like, “It doesn’t feel like enough to just email somebody their script—plays are meant to be performed.” So, I hired directors, actors, and a stage manager each year to do a showcase of the plays I wrote that year.
The reason it was called “The Dictionary Project” was because no matter what level people donated at, they chose a number between 1 and 1,555—which is how many pages were in this big dictionary I got. I did this five years in a row. By the end, I had three hundred short plays. So many of them are things that I normally would not have written, but am so glad that I did.
Q: What did you learn from the experience of producing so much quantity?
A: I learned how much you can fit on a page—physically and plot-wise—and how important each page of a story is. I learned how to establish character and setting quickly. I used: “Who’s there, what are they trying to do, and why might they fail?” You do that 300 times, and you’re like, “Okay, I got this.”
Every year, I tried to write all the one-page plays first, then the threes, then the tens. Every time I jumped up in length, I was like, “This is three times as long! How the hell am I gonna fill this page space?” Well, new things have to happen, and you have to complicate the plot. I accidentally taught myself structure in this backward way. And then, putting the plays in front of an audience was like, “Okay, I thought this would work,” or, “Hey, this is funnier than I thought it would be.”
At the beginning of the project, I was so serious, like, “Every short play will be very dramatic and important and will prove I’m an incredible writer.” And by the end I was like, “This is just a fucking fun story.” So, I learned how to be less serious as well.
Q: What is your favorite part of the creative process?
A: Since I’ve started doing more contract work—where I’m hired specifically to give someone a deliverable—my favorite part of the writing process is right after we’ve agreed on an outline and I’m doing my first draft. That first draft is me being like, “Here are all of my wild and fun ideas, this is me creating what I feel the best about. Let me try these fun things.” I’m still doing the assignment, but being like, “If you just left me to my own devices, this is what I would create.” And then when I get notes like, “Hey, we should add more characters, this isn’t working for me, this is fun but it ruins the third act,” I can be like, “I respect that, I understand. I shot my shot, let’s change this so it works better for its intended purpose.”
Q: What most inspires you as a writer?
A: What most inspires me is characters who do something that they weren’t expecting to ever do. How do you push somebody out of that comfort zone to that place? I’m also interested in characters who are radical but refuse to acknowledge that they’re radical. Maybe that’s why I love Andor so much. The play that I was talking about that’s set in the GLBT Historical Society—it’s about this guy named Oliver Sipple—called “Billy”—who saved President Ford’s life in 1975 San Francisco. I was drawn to him because he was outed by Harvey Milk and claimed by him as a gay hero. But Billy is like, “Don’t call me a hero, I’m not a hero, I just acted on instinct.” I was always interested in that with him.
I also have this 1930s pilot that’s inspired by real people, but I fictionalized it. My main character is the only female director in Hollywood in the 1930s and 40s studio system as the Hays Code is taking over. And she’s very queer. All her friends are like, “Oh great, you’re going to make feminist movies! You’re a butch lesbian! Fight the system!” and she’s like, “I’m not a feminist. I’m not a lesbian. I’m just a director, so let me keep making films.” So, it’s that battle between being who you are and staying safe and surviving. What a great push-pull to have at the center of a story.
You can stay up to date on Cassandra’s amazing projects by following her on Twitter and Instagram.
This post features the story from David Bayles and Ted Orland’s Art & Fear that demonstrates the importance of quantity in the “quality vs. quantity in creativity” debate.
New to the topic of video game writing? This ScreenCraft article introduces the basics. “Game writing really is … the only place where the writer isn’t telling their story, or the protagonist’s story, but rather the player’s story.”