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)

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.

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)

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)

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

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.

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.

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