Inactivity, lack of sleep, and poor nutrition predispose individuals to health risks. Patient-Reported Outcomes (PROs) assess physical behaviours and psychological states but are subject of self-reporting biases. Conversely, wearables are an increasingly accurate source of behavioural Technology-Reported Outcomes (TechROs). However, the extent to which PROs and TechROs provide convergent information is unknown. We propose the coQoL PRO-TechRO co-calibration method and report its feasibility, reliability, and human factors influencing data quality. Thirty-nine seniors provided 7.4 ± 4.4 PROs for physical activity (IPAQ), social support (MSPSS), anxiety/depression (GADS), nutrition (PREDIMED, SelfMNA), memory (MFE), sleep (PSQI), Quality of Life (EQ-5D-3L), and 295 ± 238 days of TechROs (Fitbit Charge 2) along two years. We co-calibrated PROs and TechROs by Spearman rank and reported human factors guiding coQoL use. We report high PRO—TechRO correlations (rS ≥ 0.8) for physical activity (moderate domestic activity—light+fair active duration), social support (family help—fair activity), anxiety/depression (numeric score—sleep duration), or sleep (duration to sleep—sleep duration) at various durations (7–120 days). coQoL feasibly co-calibrates constructs within physical behaviours and psychological states in seniors. Our results can inform designs of longitudinal observations and, whenever appropriate, personalized behavioural interventions.