Over the last 20 to 30 years, the use of mediation in Australia to resolve family disputes has grown significantly. Since the 2006 reforms to the Family Law Act 1975 (Cth), family dispute resolution, a common form of which is family mediation, has effectively become a compulsory first step in post-separation parenting disputes that enter the family law system. There are many good reasons for encouraging parties to participate in family mediation. Mediation is a flexible, cost-effective, time-efficient, more humane, less adversarial way for families to manage and resolve post-separation disputes. Family mediation is also a process that enables party self-determination, empowering the parties to determine together the best arrangements for their family into the future. However, vigilance is required if the capacity of each party to negotiate towards a mutually agreeable outcome is to be effectively sustained and the full potential of the benefits of mediation are truly to be achieved. In this article, we use Ludwig Wittgenstein’s concept of a language game and the related notion of a clash of genres to explore some of the underlying conventions and expectations that create challenges for the parties in family mediation. We then consider how mediators might respond to these challenges and the implications this holds for mediator ethics.