EP 294 — How to Navigate Dating When You’ve Been Hurt Before

from And How Does That Make You Feel? · host Jack Heyworth

Send us Fan MailHow do you open your heart again when a previous relationship left you hurt, betrayed, or afraid of getting close to someone new? In this episode, we explore what emotional pain does to the way we date, why heartbreak often creates hypervigilance and self-protection, and how old wounds can quietly influence new relationships. Learn the difference between boundaries and emotional walls, why trust is often misunderstood, and how to approach dating with both openness and self-respect. A deep dive into healing, vulnerability, and learning how to build connection without letting past hurt dictate your future.

What this episode covers

Send us Fan Mail How do you open your heart again when a previous relationship left you hurt, betrayed, or afraid of getting close to someone new? In this episode, we explore what emotional pain does to the way we date, why heartbreak often creates hypervigilance and self-protection, and how old wounds can quietly influence new relationships. Learn the difference between boundaries and emotional walls, why trust is often misunderstood, and how to approach dating with both openness and self-re...

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EP 294 — How to Navigate Dating When You’ve Been Hurt Before

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This episode is 9 minutes long.

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This episode was published on May 30, 2026.

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