We are surrounded by sensing devices. We are accustomed to them, appreciate their benefits, and even create affective bonds and might neglect the implications they might have for our daily life. By presenting Eyecam, an anthropomorphic webcam mimicking a human eye, we challenge conventional relationships with ubiquitous sensing devices and call to re-think how sensing devices might appear and behave. Inspired by critical design, Eyecam is an exaggeration of a familiar sensing device which allows for critical reflections on its perceived functionalities and its impact on human-human and human-device relations. We identify 5 different roles Eyecam can take: Mediator, Observer, Mirror, Presence, and Agent. Contributing design fictions and thinking prompts, we allow for articulation on privacy awareness and intrusion, affect in mediated communication, agency and self-perception along with speculation on potential futures. We envision this work to contribute to a bold and responsible design of ubiquitous sensing devices.