Contactless extremely high frequency connector assemblies, passive cable connector assemblies, and active cable connector assemblies are disclosed herein. In one embodiment, a contactless connector assembly can include several (EHF) contactless communication units operable to selectively transmit and receive EHF signals, and several signal directing structures coupled to the EHF CCUs. The signal directing structures can direct the EHF signals along a plurality of EHF signal pathways.