Demand response (DR) programs encourage end-use customers to alter their power consumption in response to DR events such as change in real-time electricity prices. Facilitating household participation in DR programs is essential as the residential sector accounts for a sizable portion of the total energy consumed. However, manually tracking energy prices and deciding on how to schedule home appliances can be a challenge for residential consumers who are accustomed to fixed price electricity tariffs. In this work, we present Yupik, a system that helps users respond to realtime electricity prices while being sensitive to their context and lifestyle. Yupik combines sensing, analytics, and optimization to generate appliance usage schedules that may be used by households to minimize their energy bill as well as potential lifestyle disruptions. Yupik uses jPlugs, appliance level energy metering devices, to continuously monitor the power usage by various home appliances. The consumption patterns as well as data from external sources are analyzed using data mining algorithms to infer user's preferred usage profile. Using the preferred profile as a reference, Yupik's optimization engine generates multiple usage plans that attempt to minimize energy and inconvenience costs. Some of Yupik's capabilities are demonstrated with the help of preliminary data collected from a home that was instrumented with jPlugs to monitor the power usage of a few devices.