Dogs have for long been humans’ best friend, but the human–dog relationship can be problematic. A mismatch between dogs and their keepers can lead to welfare problems for both; for example: breeding for a specific look can result in health and welfare problems and importing dogs from other countries can lead to zoonoses. In our view, many of these problems could be avoided if wannabe dog keepers reflected better before deciding to obtain a specific dog. Attempting to influence this decision, however, assumes that we know what the right choice is. In this chapter, we discuss three cases: pups with pedigrees, pups without pedigrees, and adult dogs from (foreign) shelters. We show that, in each case, certain moral assumptions are made whose legitimacy can be problematised. We conclude that the decision about what dog to obtain is not a straightforward one and that it is often difficult to establish what is actually the right choice. However, we also pinpoint certain improvements that can be made to the current system and make a number of suggestions that make the right choice the easier choice. As Anthropocene conditions may lead to the domestication of an increasing number of wild species in the future, this analysis may support reflection on the ethical implications of domestication.