Uploaded July 2026 | Updated September 2026, 2 weeks ago

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This week I'm joined by Cindy Gallop, entrepreneur, founder of Make Love Not Porn, former Chair of BBH USA, and someone who has spent her life questioning the rules we're told to live by.

⚠️A quick warning before we start: Cindy has spent her entire life saying the things most people are too afraid to say out loud, and she does so with absolutely no filter. Which, as you'll hear, is exactly what makes her so brilliant.

From challenging how we think about sex and relationships to redefining what confidence, success and fulfilment can look like, Cindy has spent decades refusing to live by anyone else's expectations. She was named Advertising Woman of the Year and has become one of the world's most outspoken voices on sex, relationships and modern culture.

In this conversation, we explore what it really means to build a life that feels true to you, rather than one that simply looks right to everyone else.

What we explore together:

* Why so many of us live by beliefs and expectations we never consciously chose
* Why confidence comes from knowing yourself, not seeking validation from others
* Why Cindy believes we need more role models for living differently
* Why the search for "the one" can stop us from asking better questions about love
* How creating Make Love Not Porn became a mission to challenge shame and misinformation around sex
* The question Cindy believes we should all ask before entering a relationship
* What it actually means to trust yourself, especially when your choices don't fit society's expectations

Love, Sarah Ann 💛

My book 'Healthy Shouldn't Be This Hard': amazon.co.uk/Healthy-Shouldnt-Be-This-Hard-ebook/dp/B0G1DHNRV5

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Chapters

00:00 Introduction
02:51 The secret of confidence
05:58 Why we struggle to promote ourselves, especially in Britain
09:08 The challenges Cindy has faced in her career
11:50 Why the conversation around sex is so negative
14:55 A different perspective on relationships
18:05 Dating as a single woman in business
21:02 Can men handle a confident woman?
24:10 Using humour to disarm difficult moments
27:10 Why Cindy stopped looking for "the one"
29:58 Friendships, family and external validation
32:57 The dating filter most people overlook
36:02 How to drown out everyone else's expectations and trust yourself
39:00 Confidence, dyslexia and self acceptance
41:50 How Cindy started dating younger men
45:01 Meeting people you'd never otherwise cross paths with
47:55 What needs to be role modelled in the real world
51:01 How Make Love Not Porn began
54:08 A story about marriage, sex and reconnecting
56:50 The noise of advice on Instagram and TikTok
59:53 An interesting topic in modern relationships
63:08 Cindy's honest take
66:08 The pressure to keep creating content
69:08 Where women are in this cultural moment