How One Podcaster Got Us Talking about Sex

Kaitlin Prest explores the messy intersections of relationships, intimacy, and love

Pair of headphones on a green backdrop
Natalie Vineberg / The Walrus

When Kaitlin Prest first came to Toronto, she worked in her bathtub. She would climb in amid piles of pillows or piles of friends, spitballing ideas that would eventually become pieces of audio art. Sometimes she wore clothes, and sometimes not, just a girl and a computer monitor and a flip chart and an artful life. Before the bathtub, her office was a bed in New York City. But one day, two summers ago, sitting on the steps of a brownstone in Brooklyn, she got a call from an executive producer at the CBC. The producer wanted to talk about an offer: come home to Canada and use the resources of a major network. It meant a chance for Prest to make the podcast series about love that had been living in her mind for many years.

Two years ago, sitting on those steps, the #MeToo movement had not yet happened, the 2015 Ontario sex-ed curriculum was still intact, and no media had yet published stories about the president of the United States explaining away sexual assault. There had been no women’s marches and surging cultural tides. But there was still so much to talk about, so much work to be done. Prest believed that people needed to have conversations about sexuality and that those conversations were often more intimate and more interesting in podcast form, as a breathy whisper in your ear. There was a love story she wanted to tell about two people being together and coming apart, about the ways we can love each other and stay true to ourselves, at least for a little while. Prest knew she had to say yes.

I meet Prest on a humid day this August, three weeks before the launch of her latest podcast, The Shadows. It’s also five weeks before she will play a recording of what the inside of a vagina sounds like as part of her keynote speech for Third Coast Festival, or the Oscars of radio. (Ira Glass, who held the honour last year, went a more traditional route.) Prest has a harried look about her. It’s the look of an artist who, for so many years, has been asking the same questions over and over of themselves about gender and love and power. Except now, others are asking them, too, and suddenly everyone is asking them, and hundreds of thousands of people are downloading her podcasts, and she’s not quite sure if any of this is real just yet.

Prest was a teenager in small-town southwestern Ontario, so her sexual education began with a combination of things: “shitty” scare tactics in gym class, bad experiences with boys, good experiences with girls, and her father’s porn stash of VHS tapes. She and her best friend also delved into the stack of smutty magazines her friend’s father kept in the garage. Other times, she and her friends would make lists of sex acts they wanted to try and then try them on each other. Years later, she started to think about the nuances of boundary drawing and consent giving and getting. And when she walked into CKUT 90.3FM, McGill University’s community radio station, at twenty-two, it felt like home. She began to volunteer, doing news stories and cutting tape for the station’s programs. And, when the trio of sex-worker hosts who ran a sex-positive, feminist show called Audio Smut decided to step down, Prest was the first to volunteer to replace them. “[It] was an anarchist station,” she says. “And they were like, ‘Cool, you’re the host.’” Here was a platform for the conversations she was constantly having with herself.

It was a heady time for Prest: she fell in love with radio, realizing that the medium allowed her to make a movie for someone’s mind in a way she’d never quite imagined before. Soon, she began making documentary, she says, that represented the realm of the erotic. “The idea of being sex positive to me at the time was really about making everyone feel safe and comfortable and celebrated in their body and in their preference,” she says. For one episode, she got her ex-boyfriend to read an erotica piece about cross-dressing. She spoke with a woman who had a sexual relationship with a dolphin. She did an episode on why our logical overrides malfunction when we’re falling in love.

After graduation, Prest moved to New York and, later on, so did her former collaborator Mitra Kaboli. The pair decided to keep making Audio Smut, parting ways with McGill’s station and instead posting their episodes online. Prest was determined to catch the attention of a bigger network. For years, old white men at conferences had told her they thought her work was pornography and that she’d never realize her dream of a mainstream network picking up her marginal, radical, queer, feminist show. She was infuriated. All of her friends talked about love and sex all of the time, she thought, so why did it seem so alien to everybody else when she did it on the air?

When Radiotopia, a podcast network that includes 99% Invisible and West Wing Weekly, among others, expressed interest, the name of Prest’s show was the first thing to go. In 2014, Audio Smut became The Heart, and suddenly, Prest’s listenership began to hit numbers that meant something in the world of broadcasting—first 50,000, then 90,000 people were downloading each episode. But Prest’s inquisitive boundary pushing stayed the same. For one episode, The Heart looked at both sides of a conjugal visit, and in another, Prest chatted with a sex worker who, once off shift and meeting with her crush, tried to explain why she didn’t want to be touched.

In one particularly compelling series of The Heart called “No,” Prest put a mic in front of her father and asked him about a time he kissed a woman he knew was too drunk to feel good about it. She put a mic in front of her male friends and her exes, and asked them why they persisted when they’d heard the word no, about times they hadn’t had consent and they went for it anyway. Hearing these men openly discuss their experiences leant the episodes an intimacy that made hearing these uncomfortable conversations a little easier. It is validating, upsetting, striking podcasting.

“As soon as I knew sex wasn’t an option, I became a bit of a dick. I got kind of cold and not really communicative,” one of her best male friends told her about an encounter he’d had. Her first love says: “I feel like probably the entire encounter, I was thinking about what I wanted more than what she wanted.” “I was like, no, she just doesn’t know better for herself.” “I just wanted what I wanted, and I wasn’t really thinking about her.” “Once you’re in that end-goal state, you’ve got a clear mission in hand. And you’re completely taken over by your dick.” “You get mad, and that’s your way of pushing,” her dad says. Prest speaks, too, giving a chilling summary of the series: “Person after person talks about pushing someone to the point where they’re tired of saying no.”

I wasn’t the only person who was affected. The “No” series was picked up by Radiolab, a US podcast with a listenership of about 1.8 million, and ran in October 2018. By then, Prest thought the consent conversation was passé—after all, she’d been having it with her friends and her peers for more than a decade. But it has only just begun.

All this has led her here, to The Shadows, CBC’s first fiction podcast. The Shadows is a story of a relationship, told in six parts, much of it in the what happens next that Hollywood’s romantic-comedy machine conveniently leaves out of its oft neat-and-tidy endings. In the series, we meet a fictional Kaitlin Prest, an artist delving into the world of puppetry. She makes money as a subway performer, busking as an accordion-playing mermaid. Fictional Kaitlin meets Charlie, a more established puppeteer, and begins to work with and learn from him. Eventually, they begin a romantic entanglement. She promises Charlie she’ll be monogamous, even though she’s not ready to make that promise. She feigns commitment while carrying on a romance with a man she meets on a train. Fictional Kaitlin struggles with where to find great love—something she has read about in so many books and watched in so many movies. Once she has it, she wonders if it’s real and, if it is, how to keep it safe.

The Shadows is both deeply raw and romantic. In it, Prest shows us that a fight about who, for example, is the light turner offer in a relationship is actually a fight about truth, deception, taking care, caring for, belonging, and the things we will or won’t do for each other. The series is a natural extension of the work she’s been doing for years, first with Audio Smut and then with The Heart: a nonlinear sex education that embraces conversations as nuanced and messy as our relationships themselves. Fiction allows her to put a finer point on some of these moments her previous work has reached for but can’t quite grasp. “My mission is to represent the realm of emotion. How do you document that? You can’t really,” she says. “In fiction, it felt easier to capture the emotional truth of a moment.” Prest knows what so many documentarians and art makers know: the story is a vehicle for the message. And the message is that talking about intimacy, openly and honestly, is a necessary and normal part of being alive.

Inside Prest’s “mermaid palace,” the bright studio where she works down the hallway from her bedroom in a rental in Toronto’s Little Portugal, are herograms—notes from friends, coworkers, and fans—written in marker on scraps of paper and taped to the wall. Below an enormous calendar, on which dates are colour coded and a legend for the colours reads, “the blood,” “the sweat,” and “the tears,” sits a stack of placards painted with golden ocean waves. Prest looks a little like a mermaid, in her blue shirt with ruffles around her shoulders, black leggings, and mismatched socks. Her hair circles her head in curls askew, like she’s risen swimming from the water to dry off in the sun. On the wall to the left of where she sits, surrounded by microphones, is a piece of paper taped up that says, in big, blocky, bold letters “Dreams.” Underneath, a single word is underlined: revolution.

“Public radio is a place where we talk about the most important things about being alive,” she says. “And we analyze them, and we talk to smart people about those things. We talk about geopolitics and policy. Why aren’t we talking about the body? Why aren’t we talking about love? Why aren’t we talking about these building blocks that make up the most important parts of our lives? Why aren’t we looking at that with the same rigorous analysis and sense of importance and legitimacy as those other things?”

When Prest and her friends started The Heart, few other programs were interrogating such feelings with quite the same rigour. The Heart is dormant now, Prest says, in part because other shows are filling the void. Turn Me On, a long-running series created and hosted by married polyamorous Halifax couple Jeremie Saunders and Bryde MacLean, explores everything from sexual orientation to trans orgasms to planning an orgy. Where Should We Begin, hosted by psychotherapist and relationship guru Esther Perel, invites listeners into her couples-counselling sessions, looking at partners contending with infidelity, impotence, child rearing, and maintaining a sexual connection. Then there’s the Savage Lovecast, by long-time sex-advice columnist Dan Savage, Modern Love, the podcast version of the long-running New York Times essay series, and Dear Sugar, a sex and love podcast co-hosted by advice columnist and bestselling author Cheryl Strayed.

After I listened to The Shadows, I realized there is another kind of education we are missing—a close read of an intimate relationship, a guide that shows us, rather than tells us, how to make and keep a love that endures. The Shadows is a coming-of-age story, a relationship choose your own adventure that shows you so many ways that could make you happy. I think we all carry the questions she asks: Can monogamy work, and should it? What kind of love—passionate and intense, or stable and enduring—is the right kind? How do you measure compatibility? What is cheating? How much do you say to your partner? How much do you not say? How do you choose between two entirely different versions of a life? When things get hard, how long do you stay? And how do you decide what it is you want, anyway, amid an ever-shifting emotional landscape?

When I leave Prest’s home and studio, three hours later, she’s already moved past these knotty questions. If there will be a second season of The Shadows, she says as she walks me down the stairs and out to her front porch, it’ll be about power. What happens, she wonders now, when you spend your whole life critiquing power and then you have some? “It feels like we’re entering a time where, for the first time ever, women have more power than they ever have. Finally!” she says, pausing for effect. “And I think now what we need to look at is how to use that power for good once we have it.”

Katherine Laidlaw
Katherine Laidlaw (@klaidlaw) regularly writes for Toronto Life and Hazlitt. She is a former senior editor of The Walrus.