A method is provided in one embodiment and includes establishing a communication session involving a first endpoint and a second endpoint that are associated with a session, the first endpoint being associated with a first identifier and the second endpoint being associated with a second identifier. The method also includes evaluating first data for the first endpoint; evaluating second data for the second point; and determining whether to initiate a calendaring activity based, at least in part, on the first data and the second data. In more specific embodiments, the method includes evaluating a first availability associated with the first endpoint; evaluating a second availability associated with the second endpoint; and suggesting a future meeting based, at least in part, on the a first availability and the second availability.