ON REALITY TV… With Dorinda Medley and Captain Sandy

How To Fail With Elizabeth Day

Sony Music

Society & Culture

4.8 • 9.4K Ratings

🗓️ 10 November 2025

⏱️ 15 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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 [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	Life's been full on lately in the best possible way. I've just wrapped up a world-win national
0:05.2	tour for my latest book. And while it's been an incredible experience, it's also been kind of
0:10.2	exhausting. And honestly, I know I'm not alone and feeling like there just aren't enough
0:14.8	hours in the day. Between work, family, friends and the general chaos of being an adult,
0:20.4	even finding time to eat
0:21.8	properly can feel like a luxury. That's where Uber Eats steps in, because let's be real,
0:28.8	adulting is a lot. Uber Eats gives me one fewer thing to worry about. It's fast, easy, and means
0:35.6	you can actually enjoy a moment of calm, even if it's just
0:38.9	flopping on the sofa in peace. So next time you're feeling like you've done just enough,
0:44.0	let Uber Eats take care of the rest. When you've done enough, order some food on Uber Eats.
0:50.3	How to Fail is partnering with Bumble to bring your second chance love stories to life.
0:56.4	Hear how this happy couple hit it off after they met on Bumble.
1:00.2	Hi Elizabeth.
1:01.8	So I got married very early to my first boyfriend and after about two years or so we just decided
1:10.6	things weren't working and we just parted ways.
1:14.3	And I needed a change after that.
1:16.2	So I decided to move to Dubai.
1:18.3	And I was there for eight years and dating life was rubbish.
1:23.9	I knew I wanted kids.
1:25.5	So when I was 28, I looked into freezing my eggs. But then when I did that,
1:30.5	the doctor told me my egg count was low and it would be hard for me to conceive. So fast forward to
1:36.9	2020, I came back to the UK for a visit and then I got stuck in lockdown. And then I started
	...

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