The unstructured conversations of students who chatted with Freudbot in his Second Life virtual office over a 32-month period were examined in order to better understand the nature of the virtual relationship between students and conversational agents (CA) as historical figures. This research builds on past work that examined these conversations in relation to previously collected non-virtual conditions in order to isolate the possible effects of virtual world immersion on the conversational record (Heller, Procter, & Rose, 2016; Heller & Procter, 2014). Forty-nine of the longest conversations were selected and analyzed using the Linguistic Inquiry and Word Count software (Pennebaker, Booth, & Francis, 2007) in order to measure indices of social presence, a construct hypothesized to underlie relationships conducive to learning. Compared to a previously reported sample of shorter conversations from the same population, the long conversations in the present study were associated with significantly more positive emotions and personal pronouns. The discussion focuses on mechanisms of rapport building for CA as avatars in virtual worlds.