The Dirty Diana series debuted at No 1 on Apple Podcasts and became a cult hit around the world. Photo / Getty Images
The writers of Dirty Diana, the podcast about a woman rediscovering her sexuality that stars Demi Moore, explain how the story improved their own sex lives too.
When the American film director Shana Feste and her childhood best friend Jen Besser dreamt up Dirty Diana, an erotic fiction podcast for women, there was only one actress they wanted in the leading role: Demi Moore. “Demi was at the top of our list,” Feste says on a video call from her home in Texas.
Thanks to Feste’s Hollywood contacts - one of her films starred Carey Mulligan, Susan Sarandon and Aaron Taylor-Johnson - she met with Moore in 2020 and the rest is history. What followed was a bold, classy and captivating six-part podcast that became a monumental success. Moore stars as Diana, a 41-year-old corporate executive who, while struggling to rebuild her sex life with her husband, secretly runs an erotic website where women divulge their deepest sexual fantasies. Attracting guest stars including Lena Dunham, Melanie Griffith and Gwendoline Christie, the series debuted at No 1 on Apple Podcasts, was nominated for podcast of the year at the Ambies, ignited a heated auction for TV rights - which Amazon won - and now, four years on, has been turned into a trilogy of novels written by Feste and Besser. The first book is released this month, with the others following in February and June. A screen adaptation is still in the works.
Did the writers expect such a positive reaction? “I think we hoped it would have listeners,” says Besser, who works as a book editor in New York. Since the podcast, the 49-year-old best friends have received countless messages from women telling them how Dirty Diana helped to save their relationship or boosted their sex life. “At the root of it, this is a story about making connections - we’re all looking for that extra bit of human connection,” Besser says. “It has been really fun to see the reaction.”
“I said to Jen, if you’re having a shitty day or want to feel good about yourself, read the comment section on the Dirty Diana podcast,” Feste says. “It’s so lovely.”
Moore didn’t just take the leading role; she also “took to it like an audio engineer” (the podcast was made remotely on Zoom during lockdown). She was the first person Feste and Besser sent the novel to and has since called it “deliciously entertaining, funny, tantalising”.
“It was just an electric match,” Feste says of her relationship with the actress. “You can’t help but be struck by how thoughtful, insightful and emotionally intelligent she is. Like, off-the-roof, sky-high emotional intelligence.”
Emotional intelligence was non-negotiable when Feste was casting for the podcast. The story is one that’s close to her heart, inspired by her marriage to the film producer Brian Kavanaugh-Jones. Besser, her best friend since the age of 11, walked her down the aisle, but not long after, and aged just 32, Feste found her sex life had ground to a halt. As a result the couple separated in 2009.
“I didn’t know who to turn to,” she says. “I felt ashamed. I’d only been married a few years and suddenly hit a point where I’d stopped having sex with my husband. I was shocked - it was the one thing that was not supposed to happen.”
As she had done throughout the rest of her life, Feste confided in her best friend. Despite living almost 3,200km away in Connecticut, Besser managed to be with her every step of the way, making daily phone calls and helping her to move out of the home she had shared with her husband. Even through our three-way video call, there’s no question about the pair’s closeness. They finish each other’s sentences in a way that only lifelong best friends can and, when speaking about Feste’s marriage breakdown, both begin to cry. This dark period ignited a curiosity about women, sex and desire they couldn’t shake.
“I wanted to write about this on a deeper level and figure out what happened for myself,” Feste says. “It felt like we weren’t talking enough about desire - how to cultivate and keep it in your marriage and what happens when you lose it. So I said to Jen, should we do this?”
The duo have been speaking to each other about sex for decades, from being young girls in sex education classes to teenagers lounging on the beach reading articles like “How to please a man in five steps” in Cosmopolitan magazine. They realised “it was always about the man’s pleasure” and the conversation continued into adulthood, as they noticed their married female friends “still tiptoeing” around discussions about sex.
“We had these notions about what a healthy marriage was and that involved how many times a week you have sex. We would all joke about it,” Besser says. “That’s some of the conversation we really want to start around this book, because I think there’s real profound loneliness in a lot of marriages … You hit a moment where you’ve drifted and it’s hard to be honest about that.”
Feste calls Dirty Diana “fun, spicy and electric”. In the podcast, domestic scenes of children’s birthday parties and clearing out the spare room become blisteringly loud orgasm soundscapes. The book is just as daring, with the story flitting between Diana buying a paint set for her six-year-old daughter to extremely graphic details about the sex she had with a former lover.
Do they ever worry about going too far? “If I worry for a second, I remind myself that I’m not giving other women enough credit,” Besser says. Feste is less confident. “I worry more but I think I was underestimating our ability to talk about this. It becomes a lot less scary because we’re having this conversation and we’re normalising it. There’s so much shame around female pleasure, around talking about female pleasure … I think the podcast gave us some bravery.”
Feste was less brave when it came to directing orgasms. She admits she “was nervous” but Moore helped to put her at ease.
“Demi just talked about [orgasms] in a very normalised, clinical way. She’s a pro for a reason - I felt really free as a director and not judged,” she says. Hearing each woman’s interpretation of an orgasm was a learning curve. “They all sounded very different. Immediately I was like, ‘Wait, that’s not what it sounds like.’ I realised I had this idea of what an orgasm sounds like from porn. I thought it had to be a big performance, like Meg Ryan in When Harry Met Sally, but it’s not that. It’s so much sexier when it’s not that.”
Dirty Diana became a talking point for women around the world, but its biggest achievement is the impact it has had on Feste’s own relationship - like Diana’s, her personal story has a happy ending. Feste originally conceived of Dirty Diana as a screenplay during her separation. She says the process helped her lose feelings of shame about sexual desire, which led to her reconnecting with Kavanaugh-Jones in 2012. After couples counselling, they are now happily married with three children and - crucially - a healthy sex life.
“It’s such a cliché question, when everybody is like, ‘Is [Dirty Diana] your own version of therapy?’ " Feste says. “But it actually has really helped me, because it forced me to talk about something that I wasn’t comfortable talking about. Everybody says you’re going to be having the best sex of your life before your kids but, ironically, it’s after three kids that we’re having the best sex of our lives.”
Besser hopes the book will “be a conversation starter for men and women”, while Feste wants “women to be inspired by Diana’s story and say, ‘I deserve pleasure and I’m not going to settle for less.’ "
How does her husband feel about their sex life inspiring a multimedia franchise? “We wouldn’t be married right now if we hadn’t gone through this process,” Feste says. “How many couples do you know [who] get married, break up, have other lovers and then find their way back to each other? It’s our story. That was the story I was so excited to tell.”
Dirty Diana by Jen Besser and Shana Feste (HarperCollins) is on sale December 4.
Written by: Roisin Kelly
© The Times of London
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