Knowing how to end and resume conversations over time is a natural part of communication, allowing for discussions to span weeks, months, or years. The duration of gaps between conversations dictates which topics are relevant and which questions to ask, and dialogue systems which do not explicitly model time may generate responses that are unnatural. In this work we explore the idea of making dialogue models aware of time, and present GapChat, a multi-session dialogue dataset in which the time between each session varies. While the dataset is constructed in real-time, progress on events in speakers' lives is simulated in order to create realistic dialogues occurring across a long timespan. We expose time information to the model and compare different representations of time and event progress. In human evaluation we show that time-aware models perform better in metrics that judge the relevance of the chosen topics and the information gained from the conversation.