The major objective of this research is to study the planar dynamical motion of 2DOF of an auto-parametric pendulum attached with a damped system. Using Lagrange’s equations in terms of generalized coordinates, the fundamental equations of motion (EOM) are derived. The method of multiple scales (MMS) is applied to obtain the approximate solutions of these equations up to the second order of approximation. Resonance cases are classified, in which the primary external and internal resonance are investigated simultaneously to establish both the solvability conditions and the modulation equations. In the context of the stability conditions of these solutions, the equilibrium points are obtained and graphically displayed to derive the probable steady-state solutions near the resonances. The temporal histories of the attained results, the amplitude, and the phases of the dynamical system are depicted in graphs to describe the motion of the system at any instance. The stability and instability zones of the system are explored, and it is discovered that the system’s performance is stable for a significant number of its variables.