This talk addresses what continues be a major issue for developers: how to structure branching conversations in ways that feature compelling gameplay, accomplish narrative goals, and support player agency. Despite making increasingly successful games, RPG developers have not fundamentally changed their approach to structuring conversations in over a decade. With RPGs becoming more "mainstream" in the eyes of publishers and the public, now is the perfect time to do so. By examining ten years of conversation tree evolution from the original Fallout to New Vegas - and many other RPGs along the way - this retrospective will analyze what has changed for the better, what's taken a turn for the worse, and what designers and writers need to do about it.