In some implementations, sensors provide sensor data reflecting user activity detected by the sensors. An event analyzer generates an unusualness score for an event associated with a user based on routine-related aspects generated from one or more user routine models associated with the user. The one or more user routine models are trained based at least in part on interaction data comprised of the sensor data. Event attributes of the event can be received that include a time of the event and attendees of the event. The unusualness score may be generated by analyzing the event attributes with respect to the routine-related aspects. The unusualness score is generated to quantify a level of deviation between the event attributes and the routine-related aspects. Service content can be generated for the user based at least in part on the unusualness score generated for the event.