How To Fail With Elizabeth Day ON REALITY TV… With Dorinda Medley and Captain Sandy
Nov 10, 2025
Dorinda Medley, a reality star from The Real Housewives of New York, shares her journey through grief and how joining the show helped her embrace vulnerability after losing her husband. Captain Sandy, the experienced captain from Below Deck Mediterranean, dives into life onboard, revealing the dynamics with her crew and the quirks of reality TV filming. Both guests explore the unexpected connections formed in the reality TV world, highlighting the transformative power of authenticity and community.
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Quick Entry Into Housewives
- Dorinda Medley describes being recruited to The Real Housewives after friends urged her to try it as a short-term role.
- She accepted easily, thinking she could be a "friend" on the show and leave if she disliked it.
The Cost Of Playing Superwoman
- Dorinda realized she had been playing "Superwoman" and avoided vulnerability after her husband's death.
- That persona blocked asking for support and expressing grief publicly.
Crafting A Social Persona In London
- Dorinda recounts moving to London, feeling isolated and studying how other women behaved to fit in.
- She performed the role of the perfect wife and mother to hide fear and loneliness.