Ecological momentary assessment (EMA) outcome measures can relate people's subjective auditory experience to their objective acoustical reality. While highly realistic, EMA data often contain considerable variability, such that it can be difficult to interpret the results with respect to differences in people's hearing ability. To address this challenge, a method for “guided” EMA is proposed and evaluated. Accompanied and instructed by a guide, normal-hearing participants carried out specific passive and active listening tasks inside a real-world public lunch scenario and answered EMA questionnaires related to aspects of spatial hearing, listening ability, quality, and effort. In situ speech and background noise levels were tracked, allowing the guided EMA task to be repeated inside two acoustically matched, loudspeaker-based laboratory environments: a 64-channel virtual sound environment (VSE) and a three-channel audiology clinic setup. Results showed that guided EMA provided consistent passive listening assessments across participants and conditions. During active listening, the clinic setup was found to be less challenging than the real-world and the VSE conditions. The proposed guided EMA approach may provide more focused real-world assessments and can be applied in realistic laboratory settings to aid the development of ecologically valid hearing testing.