The guilt, the judgment and a friendship 20 years deep: How do I know when it's time to let go?

She Rises with Ashy & Tijana · Aug 11, 2026 · 10m · transcript

On this weeks bestie advice segment, a listener writes in about a friendship more than 20 years in the making and the quiet unravelling she's not proud of. But now that her friend is thriving in so many ways, a harder feeling has crept in: resentment, frustration, judgment. She's wrestling with differing values, guilt over catching up out of obligation, and the fact that she's one of the few friends her friend has left. Her question is one so many of us are scared to ask… how do you tell the difference between a friendship worth fighting for and one you've quietly outgrown? And how do…