Automobile windshields are typically curved, creating an oblique angle of attack between the wiper blade and the windshield. This attack angle means that the wiper may jump off the windshield while wiping, causing a chattering noise and preventing the rainwater from being fully wiped off the windshield. Thus, it is important to examine the dynamics of the wiper blade under friction. In this study, the relationship between the attack angle and the jumping phenomenon is clarified through dynamic analysis. We introduce an analytical two-link model corresponding to an actual wiper blade that considers the exchange of dynamic and static friction between the windshield and the blade. The dynamic friction is assumed to be negatively correlated with the relative velocity, and the static friction is described by a set-valued function. As the motion transitions from the stick state to the slip state, the equation to be solved changes. Hence, the initial condition after a transition must agree with the final condition before the transition. Because the governing equations are nonlinear and the solution is highly dependent on the initial condition, the transition time and corresponding state variables are vital. The slack variable method is used to obtain the exact transition time and initial conditions. The sign of the normal force acting on the blade from the windshield determines the occurrence of the jump phenomenon. A larger attack angle makes the jump phenomenon more likely. However, the jump phenomenon does not occur when the motion of the blade reverses. Experimental observations support the theoretical description of the wiper blade.