A "silver tsunami" is on its way. Silver tsunami refers to the rapid aging of the population and, in particular, of the baby boomer generation. This demographic shift has moved the focus of researchers, designers, health care providers, and policymakers from ascertaining ways to extend the lifespan to ways to improve the quality of life. The aging population constitutes one of the most significant social transformations in the 21st century, making technology essential for the senior community to integrate with the outside world. However, the focus of recent research in designing technology for older adults lies in its usability and ability to monitor health. Despite the increasing number of studies in the field of aging and technology, there is insufficient research on understanding the practical issues of user focus, adoption, and engagement with respect to interactive technologies among older adults. In this study, we used four technological interventions (Move and Paint, Savi, uDraw, and GrandPad) that are new to older adults to stimulate and increase their initial engagement with technology use. We employed a mixed-method approach involving focus group discussions, in-depth interviews, observations, and diary study to understand the technology-related perceptions and behaviors of older adults and identify factors affecting their initial engagement with interactive technology. This study points out the lack of research on initial engagement among older adults and highlights the importance of the same in the use of new interactive technology. Our thesis statement is that initial engagement, which affects long-term engagement, is more important than need and usability and poses different challenges among older adults based on their behaviors toward interactive technology. The contributions of this study are 1) a new model for older adults’ engagement with interactive technology, 2) an active-passive spectrum of older adults’ behaviors toward interactive technology, and 3) the identification of key factors that influence the initial engagement of older adults. We present new expectations of initial engagement in Human Computer Interaction (HCI) and suggest new research directions in the use of interactive technology by older adults.