A communication assistance system has a first database having a plurality of listings therein, each having at least one contact name and a corresponding contact number. A device is configured to receive a directory assistance communication from a device of a user requesting at least one listing. A past requested listing table for at least one of said users is configured to store prior requested listings obtained from the database, as previously requested by the user. The past requested listing table is generated by the system and transmitted for storage on the device of the user so that when the user contacts the system, with the at least one listing stored on the past requested listing table being masked, the system may allow a communication connection between the device and the listing on the past requested listing table.