When a late-night medical emergency upended Jenny Somers’ world, fear and fragility became unexpected companions. Out of that darkness came “How Long,” a raw and prayerful song shaped by grief, healing, and the Psalms. In this episode of The Deepest Cut, the beloved folk/pop duo Jenny & Tyler open up about the story behind the song, the private ways they process pain through music, and how their art continues to trace the thin places between lament and hope.

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In this episode of The Deepest Cut, singer-songwriter Matt Wheeler reflects on the painful season that inspired his 2024 single Worn Thin. Known for crafting songs rooted in literature, Matt shares how personal trials led him to a “thin place”—a sacred space where God felt closer than ever. From health struggles to spiritual renewal, this conversation explores the intersection of suffering, transcendence, and the healing power of honest songwriting.

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On this episode of The Deepest Cut, Greg LaFollette shares the story behind Psalm 88 (Darkness is my Closest Friend)—a hauntingly honest song born from a season of deep pain. Rather than rushing toward resolution, Greg explores what it means to remain in lament, offering worship for those still in the valley. It’s a moving conversation about faith in the dark, the power of honest prayer, and creating space for sorrow in our spiritual lives.

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