In this paper, we describe the Adaptive Place Advisor, a
conversational interface designed to help users decide on a
destination.  We view the selection of destinations as an interactive
process of constraint satisfaction, with the advisory system proposing
attributes and the human responding.  We further characterize this
task in terms of heuristic search, which leads us to consider the
system's representation of problem states, the operators it uses to
generate those states, and the heuristics it invokes to select these
operators.  In addition, we report a graphical interface that supports
this process for the specific task of recommending restaurants, as
well as two methods for constructing user models from interaction
traces.  We contrast our approach to recommendation systems with the
more common scheme of showing users a ranked list of items, but we
also discuss related work on conversational systems.  In closing, we
present our plans to evaluate the Adaptive Place Advisor
experimentally and to extend its functionality.