A system includes a memory and at least one processor to receive a registration request from a first client computing device and send a response to the registration request to the first client computing device, receive a registration request from a second client computing device and send a response to the registration request to the second client computing device, receive a calendar invitation to share calendars from the first client computing device and send information associated with the calendar invitation to the second client computing device, and receive an automated calendar comparison request comprising a list of users, a period of time, and a time frame, determine a list of open times based on the list of users, the period of time, and the time frame, and transmit the list of open times.