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We describe and experimentally validate a question-asking framework for machine-learned linguistic knowledge about human emotions. Using the Socratic method as a theoretical inspiration, we develop an experimental method and computational model for computers to learn subjective information about emotions by playing emotion twenty questions (EMO20Q), a game of twenty questions limited to words denoting emotions. Using human–human EMO20Q data we bootstrap a sequential Bayesian model that drives a generalized pushdown automaton-based dialog agent that further learns from 300 human–computer dialogs collected on Amazon Mechanical Turk. The human–human EMO20Q dialogs show the capability of humans to use a large, rich, subjective vocabulary of emotion words. Training on successive batches of human–computer EMO20Q dialogs shows that the automated agent is able to learn from subsequent human–computer interactions. Our results show that the training procedure enables the agent to learn a large set of emotion words. The fully trained agent successfully completes EMO20Q at 67% of human performance and 30% better than the bootstrapped agent. Even when the agent fails to guess the human opponent’s emotion word in the EMO20Q game, the agent’s behavior of searching for knowledge makes it appear human-like, which enables the agent to maintain user engagement and learn new, out-of-vocabulary words. These results lead us to conclude that the question-asking methodology and its implementation as a sequential Bayes pushdown automaton are a successful model for the cognitive abilities involved in learning, retrieving, and using emotion words by an automated agent in a dialog setting.