This research explores mediated ritual interactions in the form of pictures taken using a mobile device in tandem with two critical designs: Probably Not and World to GIF. We take our point of departure in Rich Ling’s understanding of mobile interaction as a ritual of social cohesion and social bonding to explore sociotechnical interactions with mobile technology. By means of playful critical interaction design methods, we explore how deviance from the ritual of mediated interaction through taking pictures on the mobile phone may enhance our understanding of artificial agents. Building upon Ling’s work, we mobilize the ritual aspect of mobile communication to open possibilities for imagining alternatives of seeing the world through artificial intelligence. We conclude by arguing that playful designs in mobile communication research may allow us to disassemble and reassemble mobile apps which enables critical reflection on the role of artificial agents in mobile rituals.