This week on TOWTW Podcast, Chelsea sits down with Paul Keable, Chief Strategy Officer at Ashley Madison, for a conversation that flips everything you think you know about infidelity. Paul reveals the uncomfortable truth that men are actually seeking emotional validation while women are outsourcing their sexual needs, explores why toxic male fragility creates dead bedrooms, and explains how affair partners might be the most honest online daters. They dive into compassionate affairs for caregivers, why discretion isn't about shame but empowerment, and how the judgment we heap on complicated humans like us creates the very underground behaviors we claim to despise – because sometimes going into our pain rather than around it is exactly what transforms relationships.

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GUEST BIO:

Paul Keable is the Chief Strategy Officer at Ashley Madison, the world’s leading married dating platform. With over 20 years of experience in communications and strategy, he has helped shape the company’s global direction for more than a decade. Paul is known for his insights on love, monogamy, and how technology is transforming modern relationships, and he frequently speaks about creating safer, more authentic spaces for connection.