Disclosed is a pairing method and a pairing system for a wireless headset, the pairing method comprising: establishing, by an intermediate device, wireless communication connections respectively with a first wireless earpiece and a second wireless earpiece, and sending pairing information respectively to the first wireless earpiece and the second wireless earpiece based on the established wireless communication connections; and establishing, by the first wireless earpiece and the second wireless earpiece, a wireless communication link between the first wireless earpiece and the second wireless earpiece based on the pairing information. By the above pairing method, pairing between the first wireless earpiece and the second wireless earpiece can be realized conveniently.