Systems and methods to provide anonymous connections for a remote interaction system, such as a virtual classroom, which may allow a remote teacher and a group of remote students to have a sidebar discussion/presentation, for instance, to individually tutor the student as needed. In addition to telephonic connection, optional video/chat connections can be provided on-demand with same/different prices and time tracking indicators. Different media connections can be dynamically offered based on available bandwidth, and device capabilities of both the teacher and the student, upsell/transition from chat to voice to video, with price/charge confirmation (e.g., based on device capability, bandwidth). Connection quality can be monitored for improved billing. Pricing for individuals in a group learning setting can be dynamically determined (e.g., based on the size of the group, privacy request). Clips of interaction between teachers and students can be captured as recorded materials, searchable and/or viewable offline at different prices.