Abstract: A sleeping pillow assembly includes a pillow that has a plurality of cushions. A selected one of the cushions may support a head of a user while the user sleeps. The pillow has a pair of flattened portions and each of the flattened portions is distributed between the cushions. A selected one of the flattened portions may have an arm of the user positioned beneath the selected flattened portion. Thus, the user's arm is laterally spaced from the user's head when the user sleeps thereby inhibiting the user from lying directly on the user's arm.