This study explores self-reports of 241 older adults (aged 63-95) regarding loneliness and social disconnectedness, and the potential for information and communication technologies (ICT) and ride-hailing services to mitigate these phenomena. The samples are drawn from four older adult living communities in Maricopa County, Arizona. Lonelier older adults and older adults desiring greater social connections with friends, family, and outsiders appear to use ICT less and might benefit from ride-hailing services more than their less lonely and more socially connected counterparts. These findings are nuanced and depend on ICT device, type of ride-hailing service, and purpose of use. While desires for ride-hailing services were generally low, these services show promise in alleviating loneliness and increasing social connectedness, especially as older adults prepare to cease driving. Advice for implementing interventions and strategies to decrease the loneliness and increase social connectedness of community-dwelling older adults is elucidated and shared.