Same-sex relationship dissolution has reverberations for individuals beyond the nuclear family. This chapter discusses a lesbian-parent family, consisting of two moms and two kids—when it broke up nearly two decades ago, many other family members, including the donor and his husband, were deeply affected. This chapter reflects on this experience from the author’s perspective of a family scholar and an activist for LGBTQ family rights. In the absence of legal marriage and thus legal divorce, family lives turned out in ways that even the most careful, deliberate efforts could not anticipate nor protect. The experiences described highlight many losses and regrets, despite the intentional love and concern for all of the parents, children, and extended family members involved. These reflections on this experience are intended to honor the family as it once was and the families they have become.