When first meeting somebody, we’re faced with the challenge of “getting to know them.” Why do some questions seem to enable this better than others? In Experiment 1, participants (N=185) evaluated a large bank of conversational questions. We found that questions varied along a reliable latent dimension of interpersonal depth ranging from “small talk” to “deep” questions. In Experiment 2 (N=188), participants answered a subset of these questions along with a number of self-report personality scales. Using a language model to estimate how informative participants’ free responses were, we find that individualized personality predictions were more accurate when incorporating free responses; furthermore, responses to deeper questions supported more accurate personality inferences than small talk. Taken together, results suggest not only that responses contained the statistical information necessary to make abstract social inferences, but also that people have accurate intuitions about which conversational topics enable learning about and connecting with others.