Australia has experienced difficulties engaging with Asia-Pacific regional integration. Despite Australian attempts to punch above its weight in regional forums and to be a regional leader, it is still not regarded as a full member or as quite fitting into the region. It is an ‘awkward partner’ in the Asian context, and has experienced the ‘liminality’ of being neither here nor there. The former Rudd government's proposal for an ‘Asia Pacific Community’ (APC) by the year 2020 was a substantive initiative in Australia's ongoing engagement with Asia. It has, however, attracted a high level of criticism both at home and abroad. The main critical analysis of the proposal has focused on institutional building or architecture, or its relationship with existing regional institutions, but overlooks a host of often fraught questions about culture, norms, identities, and international power relations. The APC concept needs to be scrutinized in terms of these questions with a critical eye. This paper examines the cultural, cognitive, and normative dimensions of Rudd's proposal. It analyses four dilemmas or awkward problems that the APC faces.