Abstract: An intelligent assistant of a computing system receives a first message from a first client device. The computing system interfaces with calendar servers associated with electronic calendars associated with the possible attendees to retrieve calendar information for each possible attendee. The computing system analyzes the calendar information to identify a plurality of possible time slots for the calendar event. The computing system prompts the target user to select a time slot by sending the target user a message comprising the plurality of possible time slots. The computing system receives a selection of the time slot from the plurality of possible time slots from the target user via a reply message. The computing system identifies a subset of possible attendees associated with the time slot. The computing system, in real-time, schedules the calendar event comprising the target user and the subset of possible attendees.