This study aims at analyzing the factors that stimulate vibrant conversation and puts forth questions on what kinds of language behaviors speakers use and in what ways listeners respond in stimulating continuous conversations. To achieve this aim, this study takes a mathematical linguistic approach and compares two groups of participants, “A” group, whose conversations flow smoothly, and “J” group, which lacks continuity in conversations, by paying attention to the departure and ending points of conversations. The analytical focus is on who initiated the conversation, the persons who followed the conversation, and who spoke what in the conversations. The results of the analysis show that within the J Group, participants in the conversations were of two types, speakers who were passive participants uttering only backchannel speech depending upon the conversation topics and active ones leading the conversations. In contrast, within the A Group, there were no major differences observed among the participants in the conversations in terms of speech types. This fact indicates that the different situations in which participants join in conversations are likely to affect the possibility of making good and continuing conversations. Further study should clarify stimulating factors for good, continuous conversations from diverse perspectives.