Notifying a user about a previous conversation includes based on an analysis of the previous conversation between a first user and second user determining a characterization between the first user and the second user, in response to the first user selecting, via a user device, an option to open a subsequent conversation with the second user, notifying the first user via an alert as to the characterization of the previous conversation that the first user had with the second user before reengaging the second user in a subsequent conversation, and based on an analysis of the subsequent conversation between the first user and the second user, updating the characterization to a current characterization in a database.