Freud (1905a) famously wrote that analysing older adults— people over fifty—was not advisable and, until the past decade or so, with the notable exceptions of Erikson (1963) and King (1974), later life has continued to be relatively neglected by psychoanalytic thinkers. More recently, mercifully, this has begun to change and there have been a number of publications reflecting psychodynamic approaches to thinking about and working with older people (Davenhill, 2007; Evans & Garner, 2004; Quinodoz, 2009; Russ, 2011; Waddell, 2002). The article by Russ (2011) describes the first of two study days on working with older people provided by the Working with Older People Interest Group at the Scottish Institute of Human Relations (SIHR). Because psychoanalytic work with older people has been marginalised for so long, we have found the opportunity for interaction with others interested in such work invaluable. In this chapter, we contribute to the growing literature in this field by illustrating both the potential of working with older people individually and taking psychoanalytic thinking into institutional settings such as care homes.