Abstract: A wireless headset system (and method) for connection to a gateway such as a mobile cellular phone that includes a dock assembly and a wireless headset. The dock assembly includes a presence sensor, a first docking connector, and a circuit for sending a connection signal to the first docking connector in response to a triggering of the presence sensor. The headset includes a second docking connector for releasably connecting with the first docking connector, and connection circuitry for initiating a wireless connection with the gateway (e.g. mobile cellular phone) in response to receiving the connection signal via the first and second docking connectors. The dock assembly further includes a power connector for receiving electrical power (e.g. from a car cigarette lighter connector) and for supplying the electrical power through the first and second docking connectors and to a battery in the wireless headset.