The decision to cut off a family member is a difficult one. Estrangement is an attempt to solve a painful, systemic relationship problem. This monumental move should be deeply considered, and my collectivist approach to therapy encourages being curious about and striving to understand how the different contexts our family members—epsecially those with a generational divide—grew up and live within can impact how we show up in our relationships. Without, of course, ever dismissing the very real trauma that can precede an estrangement. In this in-depth solo episode, I explore the dynamics of cut-offs, including what both the official research and my recent social media survey have to say. Then, I offer three relational self-awareness questions for folks on both sides of the estrangement experience: those considering cutting off a family member and those who are about to be or have been cut off. These questions aim to support compassionate dialogue that increases both party’s chances of finding a solution. Whether you are the estranger or the estranged, it is my hope that this conversation will leave you with some tools and a perspective you may not have considered, one that takes each person’s lived experience into consideration and opens up the possibility of finding a middle ground between an unhealthy status quo and walking away.