Various techniques for performing contextual event scheduling with an event scheduling service are disclosed herein. In an example, data is processed at an event scheduling service, based on the use of a trained machine learning model that is specific to a user. This trained machine learning model is operated by the event scheduling service determine a proposed time and proposed scheduling parameters based on the contextual information, to identify a proposed event time and event scheduling parameters based on the model, the data indicating a user state, or external data. Further examples to evaluate user activity and identify schedule characteristics based on data inputs from a user's mobile computing device, wearable sensors, and external weather, traffic, or event data sources, are also disclosed.