With little understandings on the loneliness of older adults in residential care homes structured by social contact restrictions, the provision of person-centered care was jeopardized during the pandemic. This study employed hermeneutic phenomenology to explore the lived experiences of loneliness of this population during a 5-month period of the COVID-19 pandemic. We conducted unstructured face-to-face interviews with 15 older adults living in seven residential care homes. Thematic analysis was guided by Van Manen’s approach. The essence of loneliness was uncovered as “A deprived sense of self-significance in a familiar world contributes to older adult’s disconnection with prior commitments.” A sub-theme “From collapse to dissolution of self-understanding” revealed how COVID-19 structured their loneliness. Another sub-theme, “Restoring meanings by establishing connections with entities” illustrated the ways to mitigate loneliness during the pandemic. Activities fostering alternative self-interpretation are important to protect older adults against loneliness.