A system and method for automating proactive communication. The information for the desired contacts may be accepted from a user. A selection of contact communication frequency preferences may be received from a user. An automatic communication to one of the desired contacts may be initiated. The user may be allowed to cancel the automatic communication, in response to receiving a notification that the communication is about to begin. A response indicative of the communication status may be received. Rules and preferences may be optimized based upon the received response.