The system and method for automatically scheduling appointments includes receiving, at the appointment server system, appointment preference information from a client system associated with a user, wherein the appointment preference information includes contact details for one or more contacts of the user. In response to receiving the appointment preference information from the user, the appointment server system automatically, without human intervention, schedules a first proposed appointment based at least in part on the appointment preference information, wherein the first proposed appointment includes a first location, a first plurality of participants including the user and a first contact of the one or more contacts, and a first date that was not selected by any of the first plurality of participants. The appointment server sends an electronic message to the first plurality of participants including an invitation to the first proposed appointment.