A mechanically controllable bicycle shift operating device for operating a shifting device that selectively moves a chain between a first gear having a first diameter and a second gear having a second diameter that is smaller than the first diameter of the first gear using a guiding portion, wherein the first gear is the largest front sprocket and the second gear is the smallest front sprocket, the bicycle shift operating device comprising: an operating member (54, 56) a moving member configured to be connected to the shifting device by a connecting member; and a positioning mechanism (78, 80, 82, 84) selectively maintaining the moving member in any one of a first position that locates the guiding portion to a first guiding position where the chain corresponds to the first gear, a second position that locates the guiding portion to a second guiding position where the chain corresponds to the second gear, and a third position that locates the guiding portion to a third guiding position where the chain corresponds to the second gear, the third guiding position being farther from the first guiding position than the second guiding position, the positioning mechanism (78, 80, 82, 84) being configured such that the moving member moves in a first direction from the first position to the second position in response to a single operation of the operating member, (54, 56) the positioning mechanism (78, 80, 82, 84) being void of any position maintaining structure that maintains a position of the moving member between the first position and the second position, and wherein the positioning mechanism (78, 80, 82, 84) is further configured such that the moving member moves a first moving amount from the first position to the second position and moves a second moving amount from the second position to the third position, the first moving amount being larger than the second moving amount. an operating member (54, 56) a moving member configured to be connected to the shifting device by a connecting member; and a positioning mechanism (78, 80, 82, 84) selectively maintaining the moving member in any one of a first position that locates the guiding portion to a first guiding position where the chain corresponds to the first gear, a second position that locates the guiding portion to a second guiding position where the chain corresponds to the second gear, and a third position that locates the guiding portion to a third guiding position where the chain corresponds to the second gear, the third guiding position being farther from the first guiding position than the second guiding position, the positioning mechanism (78, 80, 82, 84) being configured such that the moving member moves in a first direction from the first position to the second position in response to a single operation of the operating member, (54, 56) the positioning mechanism (78, 80, 82, 84) being void of any position maintaining structure that maintains a position of the moving member between the first position and the second position, and wherein the positioning mechanism (78, 80, 82, 84) is further configured such that the moving member moves a first moving amount from the first position to the second position and moves a second moving amount from the second position to the third position, the first moving amount being larger than the second moving amount.