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?

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📚 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.  

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