How To Fail With Elizabeth Day10 Nov 2025

ON REALITY TV… With Dorinda Medley and Captain Sandy

If you know me at all, you’ll know that I am a huge advocate for reality TV. So what better reason to have a little trawl through my archives than to revisit some of my favourite interviews from reality TV stars? First, we hear from Dorinda Medley, known and adored from The Real Housewives of New York. Dorinda speaks about being approached to join Housewives shortly after losing her husband. She talks about her grief as a young widow and how the Bravo community supported her when she needed it most. Then, we turn to Captain Sandy from Below Deck Mediterranean. Sandy talks about life on board with production crews, the dynamics with her team, and - crucially - what she would put on her own preference sheet. Even if you’re not usually a reality TV fan, I hope this episode offers a glimpse into the humanity behind these shows - and how connection, vulnerability and growth can show up in the most unexpected places. Listen to Dorinda Medley’s full episode of How to Fail here: https://link.chtbl.com/Lf44HTRS Listen to Captain Sandy’s full episode of How to Fail here: swap.fm/l/CaptainSandy 🔗 LINKS + MENTIONS: Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @howtofailpod @elizabday TikTok: @howtofailpod @elizabday Website: www.elizabethday.org Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com 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

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