Over a number of years a number of questions in adult education have resisted a search for a more comprehensive answer. These concern, for example, the following. Firstly, adults who have returned to education frequently express their deep satisfaction with the learning experience and inform evaluators that their self-confidence and esteem has been greatly enhanced. What does this enhancement involve? Does this gain in sense of self reflect the increasing importance of credentials in the labour market, a successful adaptation to, often classed and gendered, social norms, a new form of reflexive individualism or provide more evidence of the pervasive use of therapeutic language in society ? The predominance of the theme of ‘self esteem’ in the interviews undertaken as part of an ongoing EU funded study of access and retention of non-traditional students in higher education (RANLHE, 2009) and the search for useful sensitising concepts for this research (SCUTREA, 2009) has forced us to reconsider what this refrain in student interviews might mean. With an interest in critical pedagogy we have been looking for ways of empirically deepening our understanding of what they mean when they make such observations. Secondly, having engaged in a study of the ideas of Jürgen Habermas (Fleming, 2009; Murphy & Fleming, 2006) and those of John Bowlby (2008a) we have intuitively grasped that there is a connection between Bowlby’s Attachment Theory (with the importance it gives to reciprocal and close relationships of care and security inducing attention) and Habermas’s Theory of Communicative Action on the other hand (with its imperative of engaging in discourses that are egalitarian, free and democratic). How these might be connected is an ongoing project. Thirdly, there is an ongoing need to rescue the concept of lifelong learning (Field, 2007; Finnegan, 2008; Illeris, 2004) from domination by the one-dimensional economic (neo-liberal) version in command in many policy discourses and re-establish a critical theory of lifelong learning.