Headset assemblies and headset connectors are provided. Headset connectors can include a magnetic mating face and a plurality of electrical contacts disposed within the mating face. Engaging assemblies and engaging connectors are also provided. The engaging connectors can include a housing having a mating side, a magnetic array structure, and a plurality of spring biased contact members. The magnetic array structure can be fixed within the housing and house a plurality of spring biased contact members. The spring biased contact members can include tips that extend out of the mating side. The tips can electrically couple with electrical contacts in a headset connector.