Inquiry into anticipation is framed within this chapter in a view from Anticipation Studies not only Science, accentuating cultural, constructionist and critical interpretative aspects. In this theoretical excursus, authors argue that Futures Studies needs to more fully take up a body of work from Design Studies. Drawing on various aspects of Design inquiry, the chapter provides an overview of some of the approaches that have been advanced and ways they might offer Anticipation Studies routes and means to more fully framing approaches to the making and analysis of anticipatory systems, engagements, and reflections. As designerresearchers with academic transdisciplinary backgrounds, our views are positioned from the work of others as well as via practice based research through design epistemological investigations. Design Futures remains a fruitful space for further design inflected inquiry.