An automated agent, such as an instant message robot, is be used to facilitate introduction of a chat participant to a small group of other chat participants in a chat room. To do so, for example, a BOT may present a chat participant who desires to be introduced to a small group of chat participants in a chat room with a series of multiple-choice questions, identify a subset of chat participants based on responses to the multiple-choice questions, and provide introductions among the chat participants in the subset to facilitate conversation therebetween. For example, the introductions provided by the BOT may indicate areas of mutual interest among chat participants in the subset, similar responses to one or more multiple-choice questions, and/or diverse responses to one or more multiple-choice questions.