ON REALITY TV… With Dorinda Medley and Captain Sandy

Summary

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How To Fail With Elizabeth Day

Episode: ON REALITY TV… With Dorinda Medley and Captain Sandy

Date: November 10, 2025
Host: Elizabeth Day (Sony Music Entertainment)
Guests: Dorinda Medley (The Real Housewives of New York), Captain Sandy Yawn (Below Deck)

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Overview

This special episode celebrates the world of reality TV through thoughtful conversations with two iconic Bravo stars: Dorinda Medley and Captain Sandy. Host Elizabeth Day explores their personal failures, what reality TV teaches viewers and participants alike, and offers an engaging behind-the-scenes look at the making of beloved reality programs. Whether or not you follow reality shows, this episode provides relatable insights into resilience, vulnerability, and personal growth.

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Key Discussion Points & Insights

1. The Value of Reality TV (02:10)

• Elizabeth Day passionately defends reality television, arguing it's often wrongly dismissed as "fluffy" but actually highlights human struggles and connections.
  • “What great reality TV shows do is show people navigating the ups and downs of life. It makes us feel less alone.” (Elizabeth Day, 02:15)

2. Dorinda Medley: On Joining Housewives & Learning Vulnerability

• How Dorinda Was Recruited (03:54–04:53)

  • Dorinda describes being pushed by friend Ramona to join The Real Housewives of New York.
  • The casting process was casual—"You can be a friend and if you don’t like it, you can leave. Four months of filming."
  • “I had lunch… and they were like, okay, you can be on. It was that simple. I don’t remember thinking of it as auditioning…” (Dorinda Medley, 04:37)

• Failure #1: Trying to be Superwoman (04:53–08:35)

  • Dorinda shares how the loss of her husband made her realize she'd been playing "superwoman"—afraid to show flaws or ask for help.
  • “I played superwoman so long, I forgot how to be vulnerable and allow outside people to help me.” (Elizabeth Day quoting Dorinda, 04:54)
  • She recounts her isolated move to London, trying to perfectly emulate the lives she saw around her.
  • Admits to feeling lost and angry in grief; Reality TV became a platform for vulnerability and healing.
    • “I was angry, I was lost. I felt like I got cheated… and I always thank Andy Cohen… it was a place where I was able to go through a lot of my mourning.” (Dorinda Medley, 08:35)

• On Learning to Reach Out (07:54–08:18)

  • Talks about texting a friend admitting sadness—a major step in allowing herself to show vulnerability.

3. Captain Sandy: A Peek Below Deck

• Crew Life Onboard (09:31–10:10)

  • Crew sleeps on the yacht every night; production crew sleeps off-boat and is shuttled back and forth.
  • “They have another boat that transports them to and from the hotel… the stairwells are very narrow. Like, they’re running up those stairs with those cameras.” (Captain Sandy, 10:10)

• Production Crew Challenges (10:10–10:39)

  • Describes the logistical challenges and the physical reality of filming in confined yacht spaces.

• On Firing Crew & Safety (10:39–11:07)

  • Captain Sandy emphasizes she has real authority to hire/fire, but there are legal requirements (“safe manning document”) ensuring enough certified staff for each voyage.

• Infamous Moments: Chef Mila and the Steak (11:07–11:29)

  • Recounts shocking on-board incidents, like Chef Mila licking a steak before serving.
    • “She licked a steak too. Did you see that?” (Captain Sandy, 11:14)

• Best Chief Stew Discussion (11:39–12:17)

  • Sandy acknowledges different strengths among chief stews, highlighting Natasha and others’ fine dining expertise but refusing to name a single “best.”

• Leadership and Management Lessons (12:17–13:25)

  • Emphasizes the importance of staying teachable, setting boundaries, and learning people management.
    • “To learn management skills, you have to remain teachable. To think that you know everything about everything is really ego. Your failure. Right?” (Captain Sandy, 12:55)

• Preference Sheet Wish: What Captain Sandy Wants as a Guest (13:51–14:24)

  • For fun, imagines her own “preference sheet” as a Below Deck guest:
    • “Get the grill out. Everything on the grill… grilled fish, grilled burgers, grilled steak. Yes, everything on the grill. All the toys in the water…” (Captain Sandy, 13:51 & 14:12)

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Memorable Quotes & Moments

• On Accepting Help and Being Vulnerable:

  • “After I sent it [the text], I kind of… because I sent a flaw.” (Dorinda Medley, 08:18)
  • “We connect as humans through our vulnerability. It makes you more lovable. It makes me feel closer to you…” (Elizabeth Day, 08:29)

• Behind the Scenes of Filming Below Deck:

  • “Whenever the camera comes around or we’re walking and you start to feel bad because they have to duck really fast or they run out of the camera shot. And I go, oh, my gosh, why didn’t I use the other door? Now I’m like, messing with their movement.” (Captain Sandy, 10:24)

• On Management and Growth:

  • “Maybe it’s not—You’re not here to make friends. You’re here to do a job.” (Captain Sandy, 13:21)

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Notable Timestamps

• 02:10 – Elizabeth Day’s ode to reality TV and introduction of guests
• 03:54 – Dorinda explains how she was cast on Housewives
• 04:53 – Discussion of Dorinda’s “superwoman” failure
• 07:54 – Dorinda on admitting vulnerability by texting a friend
• 08:35 – How Housewives and Bravo community supported Dorinda
• 09:31 – Captain Sandy explains crew and production logistics
• 11:14 – Captain Sandy recalls “Chef Mila” licking a steak
• 12:17 – Captain Sandy discusses management, naming crew highlights
• 13:51 – What Captain Sandy would pick for her preference sheet

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Tone & Style

Elizabeth Day’s tone is warm, curious, and celebratory of both the genre and her guests’ candor. Dorinda is open, witty, and reflective—unafraid to admit past mistakes and share her journey toward vulnerability. Captain Sandy is pragmatic, insightful, and brings a no-nonsense leadership perspective, peppered with dry humor and real behind-the-scenes revelations.

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Summary

Elizabeth Day’s exploration of “failure” with two Bravo stars peels back the entertainment of reality TV to show its deeper lessons—emphasizing growth through vulnerability and the universal human journey behind every televised moment. Whether discussing the awkwardness of adjusting to a new country, the challenges of leading a crew (filmed and unfilmed), or the importance of letting go of perfectionism, the episode is a must-listen for fans and newcomers alike.

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For exclusive insights, human stories, and plenty of reality TV fun—this episode delivers connection, laughter, and genuine wisdom.

Transcript

[Elizabeth Day]

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[Jonathan Van Ness]

It's Jonathan Van Ness from Getting Better. With Jonathan Van Ness, it's easy to feel hopeless. But we don't have to stay there. I'm all about finding places where we can turn that energy into hope and into action. One of those places is Americans United for Separation of Church and State. Americans United, or au, is this quiet but mighty force working every day to preserve freedom without favor and equality without exception. I'm so obsessed with that tagline. And let me tell you something, honey, that wall between church and state, Paper thin. It's got a leak, honey. It's one of the last safeguards protecting so many of our rights. So right now, from bodily autonomy to LGBTQ + rights to the future of public schools, to me, this is about creating a world where everyone gets to live as themselves. As long as you're not harming anyone else. Now is not the time to curl up and hide. It's the time to link arms and stand together for a better future. Join Americans United for Separation of Church and State and their growing movement. Because church, state separation protects us all. All. Learn more and join the [e-mail] better. Let's go. Americans United.

[Elizabeth Day]

Now. If you know me at all, you'll know that I'm a passionate, unapologetic advocate for reality TV. Truly, it could be my PhD subject. Now, some people might mistakenly think it's just surface level fluffy, but what great reality TV shows do is show people navigating the ups and downs of life. It makes us feel less alone. And it also entertains and provides some escapism and a break from daily routines. So this felt like a good week. To listen back to some reality TV stars who have been on how to Fail. Given that in the next few days, I am heading to BravoCon. I know, I'm so excited. And for those of you who don't know, BravoCon is is an annual fan convention hosted by the TV network Bravo, celebrating all of its reality shows and the castmates on them. And I am so excited, I can't even put it into words. First up, you're going to hear from Dorinda Medley. You'll know her from the Real Housewives of New York, and we recorded this episode in New York earlier this year. Dorinda talks about how she was recruited to appear on Housewives and the fact that she had just lost her husband at the time and how the reality TV community picked her up. Secondly, we hear from a below deck legend, Captain Sandy. Sandy talks about what it's like with production staff on board the yacht, her favorite members of the team, her favorite members of the crew, and most crucially, what would be on her preference sheet. Even if you're not currently a fan of any reality tv, I mean, who even are you? I think you'll find this a fascinating peek behind the curtain of some of the world's biggest shows. And now here's Dorinda.

[Dorinda Medley]

So, you know, Ramona was always, was a very dear friend, Luann and all of them. I always stayed in contact with them and you know, they had asked me previously to be on and I would always be in the background in scenes. I don't know if you look at.

[Elizabeth Day]

That, but don't you worry.

[Dorinda Medley]

So Ramona said to me one day, enough, like you need to do something now. And you know, it would be great. You'd be great at Housewives. I mean, you know everybody you've been on and you know us and just, just do Housewives for a year and do something because. And I thought, you know what she said, you can be a friend. You can be a friend and if you don't like it, you can leave. It's four months, four months of filming, right? And I thought so I think I kind of did. You know, it's so funny because now it's much more of a bigger process. I had lunch with Ramona and Lisa Shannon, or it wasn't even Lisa Shannon, one of the people. And they were like, okay, you can be on. You know, it was that simple. I don't remember thinking of it as auditioning and thinking of, I'm gonna do this.

[Elizabeth Day]

And your life changed and so did ours as viewers. And we're going to come back to Housewives as it pertains to one of your failures, but your first failure is playing superwoman. And as you put it to me, I played superwoman so long, I forgot how to be vulnerable and allow outside people to help me. So tell me when you first realized this about yourself.

[Dorinda Medley]

After Richard died. And that's why I could do Housewives. It all feeds because I knew that I came to New York City without a lot of money, not a lot of opportunity. And I was always. I was very careful not to show too many flaws and keep it, you know, and do everything right and follow the rules and never be unhappy, you know, and mourn privately. And, you know, it's not that I was superficial. It's just that I wanted to appear strong. I can do everything. I even remember with Ralph, you know, my first husband, who, by the way, I still love today. And he's a great guy, and he's very close to Hannah. And I attribute all of Hannah's. A lot of. Not all of Hannah's success, because Hannah owns her own success, but her success, a lot of her success in her life. Not just from me, but from both of us. But, you know, I even remember when we moved to London for the first time, I didn't know a soul. I mean, my best friends were at Peter Jones. I'd go visit people at Peter Jones at the Candle Place. There was that Florio brand, I think it was called.

[Elizabeth Day]

Yes. Yeah, it's still there.

[Dorinda Medley]

I became. I actually had lunch with them at l' Oreal one day because I just was looking for a friend, right. And, you know, I just studied how the women dressed and studied how they set tables and took a. Took a course at the Lee School and really made sure if Ralph had to go to work at 5:15 in the morning, I was up waiting for him. Made sure I knew when he came home, made sure I laid out his clothes, made sure I took on this investment banker's wife, never looking scared or unknowledgeable. Like, I watched the way lady so and so did stuff. I watched the way people, you know, dressed their children when they were in the park. So I became a study of that. And I just always was afraid that I think I could do it. No, there was no. No, absolutely. Are you tired?

[Elizabeth Day]

No.

[Dorinda Medley]

Would you throw this? Absolutely. You know, everything was. Yes, yes. And, you know, the truth of the matter is, when I look back at that now, I was afraid. I was young. I had no friends. There was no phones. I couldn't barely contact my family, you know, because there was no cell phones, no FaceTime. There were a lot of times when Ralph was thankfully working 12, 14 hours a day and gone three days a week. And I had a brand new baby that I wanted. My mother.

[Elizabeth Day]

Yes.

[Dorinda Medley]

But I couldn't do that. So I didn't reach out to a lot of people and say. And when my mother would call and be like, how are you doing? I'm like, I'm fine. It's great. It's wonderful. We just moved into Eaton Place and I'm so excited. We're going to the Venice. Like, it was all that.

[Jonathan Van Ness]

Yeah.

[Dorinda Medley]

And now I feel like I'm much more. I'm much more. Saying, I don't want that frightens me. Like, and I need your help. Can I talk to you? I even texted someone the other day and after I texted, I thought, oh, should I put that in text? I said, listen, can I. If you get time, can you call me back? I'm feeling sad today. And after I sent it, I kind of. Because I sent a flaw.

[Elizabeth Day]

Oh, well done for sending the text, first of all. And thank you so much for talking about this because it's so relatable and this is the thing. We connect as humans through our vulnerability.

[Dorinda Medley]

That's it.

[Elizabeth Day]

It makes you more lovable. It makes me feel closer to you when you do me the honor of sharing something.

[Dorinda Medley]

Like, that's what Housewives allied me. So when you go full circle all of a sudden, because I didn't really give a shit anymore, you know, And I was inside and I was still grieving for me. I wasn't great at therapy. I mean, I went to it like three times. I was like, I don't want to talk about him. Like, I wasn't great at it. And I found myself getting very insular and angry. A lot of people mourned by crying a lot and stuff. I was angry, I was lost. I felt like I got cheated, you know, so it was a great way for me to work through my really Housewives. And I always thank Andy Cohen for this. And the Bravo world, it was really a place where I was able to go through a lot of my morning. I met Carol Rozuel, who we had that incredible bonding scene with in London. I remember it opened up a bigger world and I just was able to be vulnerable and not care.

[Elizabeth Day]

I'm going to ask you some very, like, niche questions now because this is the only opportunity I'll get. Do the crew that are being filmed always sleep on the boat. Do they ever have a night off the boat during charter season?

[Captain Sandy]

No, they sleep on the boat every night.

[Elizabeth Day]

And you sleep on the boat every night?

[Captain Sandy]

Yes.

[Elizabeth Day]

Okay.

[Captain Sandy]

We wake up together and we go to. Not all together, but you know what I mean? It's just like breakfast, lunch, and dinner. You're with each other 24 7.

[Elizabeth Day]

And how does it work with the production crew? Because it's a very confined area below deck. It must. You've got all these extra people that we never see as viewers who are filming the whole thing.

[Captain Sandy]

That's right.

[Elizabeth Day]

Where do they sleep?

[Captain Sandy]

They sleep off the boat.

[Elizabeth Day]

Okay.

[Captain Sandy]

So they have another boat that transport them to and from the hotel, but at the same time, the confined spaces. Right. So the stairwells are very narrow. Like, they're running up those stairs with those cameras. And you'll see the people carrying the mic box. Whenever the camera comes around or we're walking and you start to feel bad because they have to duck really fast or they run out of the camera shot. And I go, oh, my gosh, why didn't I use the other door? Now I'm like, messing with their movement.

[Elizabeth Day]

Do you have to consult with the production when you want to fire someone?

[Captain Sandy]

No, I do, but I don't have to. But of course, they gotta line other people up because we have to require a certain amount of people on board to be able to leave the dock. It's called a safe manning document. So the insurance companies require that and the flag state requires that. I can't just drive a boat off the dock without a certain amount of crew with the certifications. Okay.

[Elizabeth Day]

I want to ask about some specific incidents. Namely, I want to ask about the chef Mila and those nutshells.

[Captain Sandy]

Now, she licked a steak too. Did you see that? Did she answer, she licked the steak.

[Elizabeth Day]

I did not see that. She licked the steak.

[Captain Sandy]

Yes. And when it was in the microwave that she microwaved, and then she smelled it and licked it.

[Elizabeth Day]

Was she actually a chef?

[Captain Sandy]

She. On her CV it said she was a chef. I believe her. I believe everyone.

[Elizabeth Day]

Yeah.

[Captain Sandy]

Until they show me otherwise. And I'm like, why did I believe them?

[Elizabeth Day]

Who, for you, has been the best chief stew you've ever worked with on the TV show?

[Captain Sandy]

The best. They all bring different elements, right? I wouldn't say the best. Natasha was very polarizing watching it with Chef Dave. But she was. She was fine dining. Yes, she was really excellent. Like, I really admired her ability to serve and the kind of service that I would want as a super yacht captain. They're all great but they all bring different elements, so I don't really have.

[Elizabeth Day]

I thought you did a great job of managing Frasier in the last season and you ended up. It felt like the two of you with such mutual respect.

[Captain Sandy]

Yes. You know, when I come as a captain, I come with years of experience with former crew. Some of the best crew. I had a chief stewardess who served the Queen of England. Like, she's the finest. Like, apart from the TV show, she was Irish Aoife, and she was my chief Stewart. And I actually had a client complain about her that she was too formal. I go, that's a great complaint. I mean, it's okay, you know, so Fraser, I see that he didn't have a lot of experience. It was really about that. And when you don't know how to manage people, that's really a disservice to the client and to yourself. To learn management skills, you have to remain teachable. To think that you know everything about everything is really ego. You're failure. Right. So sometimes you just have to let them know. No, that's not how you do it. Maybe it's not. You're not here to make friends. You're here to do a job.

[Elizabeth Day]

I want to go back to your life before you got into the maritime industry. In a minute. But just finally on the below deck, questions, have you ever imagined. So again, for anyone who hasn't watched it, the clients come and the primary will give a preference sheet and say their life likes and dislikes and that they want an all white dressed theme party, an 80s disco, and they can't eat gluten. What would be on your preference sheet?

[Captain Sandy]

Oh, my gosh. I would say get the grill out.

[Dorinda Medley]

Okay.

[Captain Sandy]

Everything on the grill.

[Elizabeth Day]

Yeah.

[Captain Sandy]

You know, honestly, I love grilled food and I would. All the toys in the water, the slide.

[Elizabeth Day]

I'm desperate to try that slide. I know that the deck crew always hate having to put it out, but.

[Captain Sandy]

Yeah, so I would be in the water the whole time and then want to come out and eat grilled food.

[Elizabeth Day]

Okay.

[Captain Sandy]

Grilled fish, grilled lobster. Like I'm not a lobster. So grilled fish, grilled burgers, grilled steak. Like, yes, everything on the grill.

[Elizabeth Day]

Please do follow how to fail to get new episodes as they land on Apple podcasts, Spotify, Amazon Music, or wherever you get your podcasts. Please tell all your friends this is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening. And Doug, here we have the Limu Emu in its natural habitat, helping people customize their car insurance and save hundreds with Liberty Mutual. Fascinating. It's accompanied by his natural ally, Doug.

[Dorinda Medley]

Uh, Limu. Is that guy with the binoculars watching us?

[Elizabeth Day]

Cut the camera. They see us.

[Jonathan Van Ness]

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[Dorinda Medley]

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