Within the EU-funded COMPANIONS project, we are working to evaluate new collaborative conversational models of dialogue. Such an evaluation requires us to benchmark approaches to companionable dialogue. In order to determine the impact of system strategies on our evaluation paradigm, we need to generate a range of companionable conversations, using dialogue strategies such as `empathy' and `positivity'. By companionable dialogue, we mean interactions that take user input of some scenario, and respond in a manner appropriate to the emotional content of the user utterance. In this paper, we describe our working Wizard of Oz (WoZ) system for systematically creating dialogues that fulfil these potential strategies, and enables us to deploy a range of potential techniques for selecting which parts of user input to address is which order, to inform the wizard response to the user based on a manual, on-the-fly assessment of the polarity of the user input.