A vehicle chatroom server includes at least one network interface configured to communicate with passenger terminals, at least one processor connected to communicate through the at least one network interface, and at least one memory storing code that is executed by the at least one processor to perform operations. The operations include obtaining passenger information and characterizing potential passenger discussion interests based on the passenger information. The operations identify a grouping of passengers who satisfy a common interest rule based on the potential passenger discussion interests. The operations then communicate with passengers in the grouping through a computerized chatbot module providing natural-language text and/or computer synthesized speech that is provided to the passengers in the grouping to invite to a discussion-focused chatroom hosted by the chatroom server. Related methods and computer program products are disclosed.