After a long, successful career as the author of an esoteric newspaper column, "Rambling With Milton," Jock Petitte finds himself unfulfilled and at loose ends. Two failed marriages have not diminished his romantic ideals or his youthful desire to become an actor, so he begins to compose one-man plays based upon historical events and to perform them at senior centers and retirement homes.

Prudence Rogers, beautiful and intelligent, has struggled with clinical depression and chronic anxiety throughout her life. When Jock meets her at the rehabilitation facility where she is recovering from an overdose and he is performing a Christmas play, he is instantly smitten. Rambling with Milton is the deeply touching story of their romance and their attempt to save each other and themselves.