Provided are a server, a method of controlling a server, and a program that can increase the variations on methods for acquiring an item or the like and enhance interest in a game. Included are receiving, from a user, an item change request for changing first item data; displaying, to the user, a selection screen to display a plurality of options after receiving the item change request; and providing the user with second item data when a selected option on the selection screen is a correct answer.