A system for a healthcare provider to administer a portable interactive hearing assessment is provided. The system allows the healthcare provider to administer the hearing assessment in a way that accurately detects hearing loss and provides recommendations for seeking further assistance from qualified hearing health specialists and/or an ENT physician. The system includes a hearing test device, and a processor that receives and processes a pressure test result associated with each of the patient's ear from a tympanometer and the patient's response to one or more pure tone frequencies transmitted by the hearing test device. The processor may also provide a report and recommendation based on received pressure test result and the determined hearing results, and demonstrate effects of any hearing loss to a person accompanying the patient so that the accompanying person understands a scope of the patient's hearing loss.