A communication system and method for routing communications can include a communication device that is configured to route a communication connection based on empirical data relating to an attempted communication. For instance, in some embodiments the device of a communication system can be configured to utilize stored and classified empirical data for automatically determining a subject of an attempted communication made by a user via the user's communication terminal and dependencies the user for that attempted communication may have on a callee for use in establishing a connection for the caller based on the determined dependencies and determined subject of the attempted communication. Information regarding the determined subject of the communication attempt can be based on the stored empirical data. The attempted communication can also be rerouted to another user based on the empirical communication data if that attempted communication is not established within a pre-selected time period.