Aboriginal individuals – often men – who went with the colonists on their travels in colonial New South Wales performed various, often vital, roles. While this is well known, less attention has been paid to the ways in which relationships developed between the colonists and those guiding, or how these relationships were dependent on meeting the needs and desires of all involved. By teasing apart some of the earliest, shakiest beginnings of Aboriginal men travelling with and ‘guiding’ the colonists, this article suggests that guiding was negotiated from the outset – the product of intercultural dialogue and deliberation – and that it is a phenomenon that benefits from being more fully contextualised.