This paper explores how known machine learning techniques can be applied in unique ways to simplify software and therefore dramatically increase its usability. As software has increased in popularity, its complexity has increased in lockstep, to a point where it has become burdensome. By shifting the focus from the software to the user, great advances can be achieved by way of simplification. The example problem used in this report is well known: suggest local dining choices tailored to a specific person based on known habits and those of similar people. By analyzing past choices and applying likely probabilities, assumptions can be made to reduce user interaction, allowing the user to realize the benefits of the software faster and more frequently. This is accomplished with Java Servlets, Apache Mahout machine learning libraries, and various third party resources to gather dimensions on each recommendation. / text