As an inevitable process, the number of older adults is increasing in many countries worldwide. Two of the main problems that society is being confronted with more and more, in this respect, are the inter-related aspects of feelings of loneliness and social isolation among older adults. In particular, the ongoing COVID-19 crisis and its associated restrictions have exacerbated the loneliness and social-isolation problems. This paper is first and foremost a comprehensive survey of loneliness monitoring and management solutions, from the multidisciplinary perspective of technology, gerontology, socio-psychology, and urban built environment. In addition, our paper also investigates machine learning-based technological solutions with wearable-sensor data, suitable to measure, monitor, manage, and/or diminish the levels of loneliness and social isolation, when one also considers the constraints and characteristics coming from social science, gerontology, and architecture/urban built environments points of view. Compared to the existing state of the art, our work is unique from the cross-disciplinary point of view, because our authors’ team combines the expertise from four distinct domains, i.e., gerontology, social psychology, architecture, and wireless technology in addressing the two inter-related problems of loneliness and social isolation in older adults. This work combines a cross-disciplinary survey of the literature in the four aforementioned domains with a proposed wearable-based technological solution, introduced first as a generic framework and, then, exemplified through a simple proof of concept with dummy data. As the main findings, we provide a comprehensive view on challenges and solutions in utilizing various technologies, particularly those carried by users, also known as wearables, to measure, manage, and/or diminish the social isolation and the perceived loneliness among older adults. In addition, we also summarize the identified solutions which can be used for measuring and monitoring various loneliness- and social isolation-related metrics, and we present and validate, through a simple proof-of-concept mechanism, an approach based on machine learning for predicting and estimating loneliness levels. Open research issues in this field are also discussed.