The table-top play situation offers unique opportunities for approaching real-world personal problems in ways where the structures inherent in the problems can be deconstructed, examined, and understood. This paper presents design considerations from the ongoing development of a therapy board-game; how every-day issues can bleed in and out from framed play sessions, and how game rules in this context can benefit from being malleable. The paper also offers a tentative avenue towards how play sessions, in a combination of stances for the design of game mechanics with approaches to game mastering, can be constructed as safe-spaces, affording players to draw near deeply personal issues and find ways to support each other.