Dorinda Medley on Grief, Identity and The Real Housewives: ‘I was angry. I was lost. I felt like I got cheated.’

Dorinda Medley on Grief, Identity and The Real Housewives: ‘I was angry. I was lost. I felt like I got cheated.’

Author: Elizabeth Day and Sony Music Entertainment July 23, 2025 Duration: 43:33
What happens when the life you thought you’d built - the one with love, money, recognition - seems to slip away? This week, Elizabeth speaks to Dorinda Medley, author, TV personality and iconic former Real Housewife of New York, about reinvention, resilience and learning to be okay with not being liked by everyone. Dorinda opens up about the loss of her husband, the loneliness that followed fame, and why her departure from Housewives was both painful and necessary. This is a raw, funny, emotional conversation with a woman who’s lived many lives - and isn’t afraid to talk about all the ways they’ve fallen apart. ✨ IN THIS EPISODE: 00:00 Intro 02:12 Life After Reality TV 03:30 Authenticity and Public Perception 06:37 Dealing with Grief and Loss 14:06 Finding Strength in Vulnerability 19:14 The Impact of Fame 21:56 Housewives' First Visit to Blue Stone Manor 23:03 Behind the Scenes Drama 23:32 Staying Connected with Castmates 25:36 Dealing with Trolls and Haters 29:00 Coping with On-Screen Conflicts 31:19 Reflecting on the Housewives Experience 32:48 Blue Stone Manor Tag Sale 35:57 Life Lessons and Moving Forward 💬 QUOTES TO REMEMBER: “A lot of people mourn by crying. I was angry. I was lost. I felt like I got cheated.” “If you want to love me, great. If you don’t, I’m okay with that.” “There’s a difference between missing Housewives and wanting to do it again.” 🔗 LINKS + MENTIONS: Join our community of subscribers here: https://howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com  Join Elizabeth at an upcoming one-off show at Cadogan Hall on 21 Sep for her new novel One of Us: ⁠https://www.fane.co.uk/elizabeth-day  Watch How To Fail on YouTube: https://www.youtube.com/@HowToFailPodcast  Instagram: @howtofailpod / @elizabday TikTok: @howtofailpod / @elizabday Elizabeth’s Substack: https://theelizabethday.substack.com/ 💌 LOVE THIS EPISODE? Subscribe to How To Fail on Spotify, Apple or wherever you get your podcasts Leave us a 5⭐ review – it helps more people discover these conversations Share this episode with someone navigating grief or reinvention 📚 WANT MORE? Stanley Tucci on grief, identity and the taste of memory https://listen.sonymusic-podcasts.link/pbegMUD1?at=1010l396Y Miriam Margolyes on fame, failure and finally giving fewer f*cks https://listen.sonymusic-podcasts.link/PJdd42Bp?at=1010l396Y Mo Gawdat on how to solve for happiness https://listen.sonymusic-podcasts.link/RhEwJYA2?at=1010l396Y Production & Post Production Coordinator: Eric Ryan   Studio Engineer: Sam Bair  Sound Engineer: Matias Torres Assistant Producer: Suhaar Ali Senior Producer: Hannah Talbot Executive Producer: Carly Maile How to Fail is an Elizabeth Day and Sony Music Entertainment Production.   Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

There's a quiet revolution happening in how we think about success, and How To Fail With Elizabeth Day is right at the heart of it. This isn't about schadenfreude or wallowing in misfortune. Instead, Elizabeth Day has created a space where the most interesting conversations begin with a simple, radical premise: our lowest moments are often our greatest teachers. Each episode, a guest-from celebrated artists and thinkers to everyday people with extraordinary stories-sits down to examine three significant failures from their own life. The magic lies in the excavation, as Elizabeth guides the discussion toward the unexpected wisdom and resilience that emerged from those setbacks. You'll hear the raw honesty in their voices, the laughter that comes with hindsight, and the profound clarity that failure can uniquely provide. This podcast, presented by Elizabeth Day and Sony Music Entertainment, digs into the messy, human stuff of life that connects us all, transforming shared vulnerability into a source of collective strength. It’s a reminder that the path to any meaningful achievement is rarely a straight line, but a series of instructive detours. The show actively invites listeners to reflect on their own stories, fostering a genuine community around the idea that we can all succeed better by understanding where we've previously stumbled. Tune in for conversations that are as comforting as they are challenging, and which might just change your perspective on what it means to live a well-lived life.
Author: Language: English Episodes: 100

How To Fail With Elizabeth Day
Podcast Episodes
ON WRITING... With Salman Rushdie and Kazuo Ishiguro [not-audio_url] [/not-audio_url]

Duration: 24:18
Welcome to another special edition of How to Fail, where I revisit conversations from the How to Fail archives. Each week, we shine a light on a particular theme, hopefully offering inspiration, perspective and comfort t…
ON GRIEF… With Mo Gawdat and Bonnie Tyler [not-audio_url] [/not-audio_url]

Duration: 13:28
Welcome to the newest evolution of How to Fail! Each week, I’ll be diving into the archives to spotlight key themes that have come up throughout my conversations with How to Fail guests. I’ll be sharing bite-sized takeaw…
Robin Wright on ageing, confidence and the myth of being ‘too late’ [not-audio_url] [/not-audio_url]

Duration: 49:50
‘I didn’t think I had that confidence, so I turned those roles down.’ Robin Wright is the legendary star of The Princess Bride, Forrest Gump, House of Cards, and Amazon’s gripping new thriller The Girlfriend. An Emmy-nom…
ON HEARTBREAK... With Alain de Botton and Jay Shetty [not-audio_url] [/not-audio_url]

Duration: 15:17
Welcome to this brand-new concept for How to Fail – where I dive into the back catalogue of the How to Fail archives, highlighting specific themes each week to bring you bitesize takeaways! Hopefully these episodes can b…
Tom Ellis - Fatherhood, Surrogacy and Years of Therapy [not-audio_url] [/not-audio_url]

Duration: 49:40
You may know Tom Ellis as the devilishly charming lead in Netflix’s Lucifer, or as the lovable Gary in the BBC sitcom Miranda. He's also made waves in the U.S., starring alongside Gina Rodriguez in Players, and appearing…
Failure Throwback: Jameela Jamil [not-audio_url] [/not-audio_url]

Duration: 58:34
Jameela Jamil is an actor, activist, and founder of the I Weigh movement. From teaching English to starring in The Good Place, Jameela shares the highs, lows, and radical honesty that define her journey. This episode fir…
Failure Throwback: Glennon Doyle [not-audio_url] [/not-audio_url]

Duration: 1:07:01
Author of Untamed and fierce truth-teller Glennon Doyle joins me for a raw and revelatory episode, first recorded in July 2020. We dive into: Why we chase approval instead of trusting our inner voice Her struggles with b…
Failure Throwback: Chimamanda Ngozi Adichie [not-audio_url] [/not-audio_url]

Duration: 1:08:02
This week we revisit one of my all-time favourite guests: Chimamanda Ngozi Adichie, recorded in July 2021. Best known for Americanah and her globally resonant TED Talks, Chimamanda opens up about the profound grief of lo…
Sir Tony Robinson - ‘I learned comedy as a defence mechanism’ [not-audio_url] [/not-audio_url]

Duration: 49:45
Recorded with a live audience in Cambridge, this captivating conversation delves deep into the life and career of a cultural force of the last half-century. Known of course for his iconic role as Baldrick in Blackadder,…