Abstract: An information processing system, a server, a user terminal, an information processing method, and a program capable of effectively realizing psychological exchanges among users is provided. A user terminal 110 includes a terminal-side display control unit 113 that generates a first flower image corresponding to a first user, a display unit 111 that displays an image generated by the terminal-side display control unit 113, and an input unit 112 that receives a first input operation by the first user. The terminal-side display control unit 113 changes the first flower image according to the first input operation.