This chapter highlights the attitudes and practices of midlife adults surrounding the act of connection on social media platforms. Employing data gathered from in-depth interviews of social media users between the ages of 45 and 65 years. It explores the social strategies that are used, often in combination, as processes of social boundary regulation. The chapter explores the findings related to privacy negotiation, boundary control strategies, and perceptions related to Internet and social media use. Flexible boundaries allow individuals to change the physical time and location in which a role is enacted; permeability refers to the degree to which an individual physically located in one domain must be psychologically concerned with another. The process of managing social boundaries, boundary work, involves the integration, or blurring, of role boundaries as well as the segmentation, or separation, of roles and environments. Some connections form bridges between the environmental boundaries that an individual establishes.