A server includes a session management device establishing a video call session between a first electronic apparatus of a first user and a second electronic apparatus of a second user, a communication device receiving match satisfaction calculated from the first electronic apparatus through the video call session, an image analysis device obtaining first feature point distribution information from a face image of the first user and obtaining second feature point distribution information from a face image of the second user, a processor training a machine learning model by using the first feature point distribution information, the second feature point distribution information, and the match satisfaction and estimating the match satisfaction of the first user for each of standby users by using the trained machine learning model when a video call connection between the first electronic apparatus and the second electronic apparatus is terminated, and a user management device selecting a third user, who becomes a next video call counterpart of the first user, from among the standby users by using the estimated match satisfaction.