An automated telephone dialing system. The system enables a handheld PID to automatically dial a telephone number stored its memory by interacting with a telephone. The telephone is equipped with a wireless port for short-range wireless data transfer. Similarly, the PID is equipped with a wireless port for short-range wireless data transfer. The PID establishes a wireless communication with the telephone. The PID is configured to control the telephone via the wireless communications such that the telephone dials a telephone number stored on the PID. The telephone number can be dialed in response to the user interacting with application executing on the PID. The application can be a contact management or address management program. The user can interact with the program, select a contact, address, phone number, or the like, through a GUI of the PID, and have this number automatically dialed by the telephone. In this manner, the user's PID seamlessly interacts with the user's telephone to dial numbers and establish phone calls without requiring the user to access controls of the telephone. The wireless communication between the PID and the telephone can be compatible with a version of the Bluetooth specification. The wireless communication between the PID and the telephone can also be compatible with a version of the IrDA specification.