Abstract: A System and Method for Facilitating Therapeutic Communication includes hyper matching a caller wishing to discuss personal issues to a sympathetic listener who has experience with the discussion topic chosen by the caller. Hyper matching includes audio recordings of listeners who are pre-screened by the system according to user metrics, that are available for caller review to further match the caller to a preferred listener. A recording of the call is available for review by pre-matched listeners ensuring two-way matching. An intelligent assistant is capable of monitoring a caller-listener conference interaction and providing real time feedback to the listener in a mentoring process. Identities of the caller and listener are shielded to protect all participants.