In this article, the authors discuss the light and dark side of attachments and attachment style in physical and digital worlds. They argue that many games offer opportunities for the generation of new and meaningful attachments to both physical and digital others. They discuss two "fundamental attachment errors" and show how these can lead to both "light" outcomes, in terms of opportunities to learn more secure attachment patterns, and "dark" outcomes, where existing dysfunctional behaviours become more pronounced. The authors argue that the avatars which children adopt online have important consequences for their psychosocial development, and that these are mediated through the degree to which the real self is differentiated from the avatar. It is proposed that attachment is a key force in understanding play, and that studying its manifestations and effects in digital playscapes may contribute to understanding the effects of life online, and how insecure attachments may become secure.