With the proliferation of rich Internet applications and interactions more closely aligned with how people think, we face some interesting challenges: * Do we design for one common audience and common tasks, or tailor applications around specific audiences and their unique activities? * How do we resolve the tension between creating simple applications that ‘do less’ and the demand for new features that some people really do need? * As we move beyond usability to create desirable interfaces, how do we handle a subjective domain like emotions? These types of challenges could all be addressed by creating a truly ‘adaptive' interface. More than removing unused menu options or collaborative filtering, this would include functionality that is revealed over time as well as interface elements that change based on usage. Imagine the web-based email client that begins offering three forms fields for attachments instead of the default one, because it 'noticed' that you frequently upload more than one file. Or the navigation menu that disappears because it is not relevant to the task at hand. Sound scary? Look at the world of game design, where inconsistency has never been an issue and where users learn new functions over time, as needed. In the same ways that ads are becoming more targeted around context and behavior, we can also create interfaces that respond, suggest, or change based on actual usage data. While much of this is still speculative, we'll explore some concrete examples of how such ideas have already been used, and other instances where they could be used. We'll also take a brief look at what technologies might support these interactions, as well as some of the rules engines that might make this possible. And, to ground this in the past, we'll at some existing navigational theories and research that might support this argument for an interface that is truly conversational and context aware.