In this project, we’re exploring the potential of leveraging existing calendar application to create a web-based digital nudging service that helps its users increase productivity level. At a higher level, we are making use of our users’ free time on the calendar and nudging them to plan calendar events on tasks they’re committed to complete such as working on ”homework assignments” or ”side projects”. Therefore, upon our study participants granting us access to their calendar usage history, we implemented and experimented on a number of different methods that attempt to analyze users’ interests and deliver personalized nudges in terms of the timing to nudge each individual and the event suggestions that would interest them. To evaluate this approach, we recruited participants with whom, after using our services, the goal is to not only incentivize them to schedule more productivity-related events on their calendars but also nourish the awareness of the productivity values calendar provides and organically increase their calendar usages.