We used in-depth interviews with 101 participants in the East York section of Toronto, Canada to understand how digital media affects social connectivity in general—and networked individualism in particular—for people at different stages of the life course. Although people of all ages intertwined their use of digital media with their face-to-face interactions, younger adults used more types of digital media and have more diversified personal networks. People in different age-groups conserved media, tending to stick with the digital media they learned to use in earlier life stages. Approximately one-third of the participants were Networked Individuals: In each age-group, they were the most actively using digital media to maintain ties and to develop new ones. Another one-third were Socially Bounded, who often actively used digital media but kept their connectivity within a smaller set of social groups. The remaining one-third, who were Socially Limited, were the least likely to use digital media. Younger adults were the most likely to be Networked Individuals, leading us to wonder if the percentage of the population who are Bounded or Limited will decline over time.