In one embodiment, a predictive contextual transaction scoring system receives transaction review data associated with person-to-person transactions from a marketplace, the transaction review data including feedback information relating to the person-to-person transaction. The system identifies contextual characteristics of the person-to-person transactions by analyzing the feedback information related to the person-to-person transactions. The system pairs a first party requesting a service to a second party providing the requested service by matching a contextual characteristic of the first party to a contextual characteristic of the second party. The system also predicts a transaction score for a new person-to-person transaction involving the first party and the second party, and provides the predicted transaction score to the marketplace to facilitate pairing of the first party requesting the service.