Abstract: Recent data-driven conversational models are able to return fluent, consistent, and informative responses to many kinds of requests and utterances in task-oriented scenarios. However, these responses are typically limited to just the immediate local topic instead of being wider-ranging and proactively taking the conversation further, for example making suggestions to help customers achieve their goals. This inadequacy reflects a lack of understanding of the interlocutor's situation and implicit goal. To address the problem, we introduce a task of proactive response selection based on situational information. We present a manually-curated dataset of 1.7k English conversation examples that include situational background information plus for each conversation a set of responses, only some of which are acceptable in the situation. A responsive and informed conversation system should select the appropriate responses and avoid inappropriate ones; doing so demonstrates the ability to adequately understand the initiating request and situation. Our benchmark experiments show that this is not an easy task even for strong neural models, offering opportunities for future research.