In July 2015 the well-known affairs Web site, Ashley Madison, was hacked and both customer details and internal company correspondence were stolen, and later dumped online for public access. In the analysis of the data, it became clear that the site had extensively used bots to attract customers. This paper brings together these bots with a short story by Candas Jane Dorsey about the discomfiting potential of human-machine intimacies. I use the two to help me explore what I argue is an inbuilt and little discussed expectation/requirement of “authentic” intimacy: humanness.