A method and system for scheduling or re-scheduling calendar events is described. One aspect of the invention involves: receiving a calendar search request to schedule a calendar event including at least one participant and a time of meeting constraint; obtaining information identifying one or more preferences associated with the at least one participant, at least one of the preferences based on the at least one participant's historical calendar activity over a predetermined period of time; searching one or more databases in a calendaring system to obtain a set of candidate calendar events that meet at least a subset of the plurality of constraints; ranking the set of candidate calendar events based on the plurality of constraints and the one or more preferences; and preparing for presentation at least a subset of the ranked set of candidate calendar events, each candidate calendar event including a specified start time.