The present disclosure provides systems, apparatuses, and methods for use of wearable electrode assemblies. The electrode assemblies improve comfort by providing increased overall surface area of their bottom surfaces, which make contact with the patient's scalp and hair. Collapse, compression, or telescoping of the bottom surface will thereby decrease the direct force and/or pressure applied by the distal member or members of the bottom surfaces to the skin. This may be advantageous in patients who have little to no hair in electrode contact areas, patient populations that are particularly skin-sensitive, and/or patients which must wear the electrode assemblies of an extended time period. The electrode assemblies further include structures to dispense and/or maintain conductive gel placed over the patient's skin, thereby maintaining electrical connection quality, and/or to facilitate the clearing of skin and/or hair prior to establishing an electrical connection.