To provide a photographing instruction system in which in a state that a student needs an advice by an instructor during photographing immediately at the spot, an instructor matching with the need of the student is selected and presented without imposing time and labor on the student's task.

A client device 200 acquires, when an instruction request is received from a student, image data associated with a picture photographed by the student so as to send it to a server device 140. The server device 140 includes: an image data analysis part 143 for analyzing image data transmitted from the client server 200 so as to set a selection condition for selecting an instructor; instructor selection part 144 for selecting an instructor out of instructor candidates registered in a database 148 on the basis of the selection condition set by the image data analysis part 143; and a system information processing part 147 for establishing communication between a terminal device used by the instructor selected by the instructor selection part 144 and the client device 200.