In this chapter, the author shares the experiences of a family who worked through two gender transitions with teachers and principals at their suburban French Catholic elementary school. Max describes his experience of transitioning as a parent at his children’s elementary school. Max was very satisfied with the way his son’s daycare teacher opened up a conversation about families in her classroom. The teacher provided the children with a variety of dolls and figures and let them tell each other who was in their family. This gave Max and Ryan’s son the opportunity to talk about his two papas, and another child to talk about their two aunts. The children were given a space to listen to each other talk about their families in ways that made sense. The work Max and Ryan did with their children’s school when Max transitioned in April 2016 ended up being very important the following summer when their daughter came out as a transgender.