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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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We all have those 2 a.m. moments—the questions that swirl in our minds when everything feels quiet but our thoughts are loud. This week, Heather leads the conversation with raw honesty about a question she once wrestled with deeply: “What is wrong with me?”
Before her infidelity, she remembers lying awake wondering why she was even entertaining the idea of another life—another marriage—something “different.” She shares what she wishes she could say to you if she could sit in your thoughts during those restless nights, especially in a world where social media constantly whispers, “You deserve more.”
After betrayal, that same question turned darker: “How could I have done something so horrific?” Heather opens up about the shame, guilt, and self-condemnation that can feel crushing after failure—and how she learned to hear truth instead of lies in those moments.
If you’ve ever questioned your worth, your sanity, or your faith in the middle of the night, this episode is for you. You’re not broken beyond repair. There is hope, even at 2 a.m.
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