Self-loosening of bolts owing to external forces occurs in several machines that are clamped by bolts and nuts. This study focuses on the self-loosening of the aiming bolt of the head lamp in a vehicle. It is important to prevent the aiming bolt from self-loosening as it has a decisive effect on the angle of the head lamp. A nut clamped with a bolt, known as a retainer, is made of plastic and has a partial screw thread. In addition, a transverse load has a considerable impact on the self-loosening of a bolt. We concentrate on the self-loosening of a bolt by a transverse load. The aim of this study is to define the limits of the external force that loosen the bolt. Based on the above conditions, we derive a theoretical equation and develop a numerical analysis program that can calculate the limiting forces for self-loosening. To verify the developed program, we design a test device that can measure the self-loosening by applying sliding forces to the aiming bolt. Using this method, we can draw the following conclusions. First, the developed testing device is suitable to prove the theory for calculating the self-loosening force. Second, the equation confirms the relationship of bolt self-loosening between resistance torque and shear force. Finally, the equation obtains the minimum value of the resistance torque required to decrease the change in the angle of the head lamp, thereby improving the possibility of increasing the stability of the head lamp.