The title refers to Indian summer, the informal expression given to a period of sunny, warm weather in late October or early November, after the leaves have turned following an onset of frost but before the first snowfall.
Gladys Cooper and James Gleason had secondary but important roles in The Bishop's Wife (1947). She was the wealthy widow, Agnes Hamilton, donating to the church conditionally, while Gleason was Sylvester the cab driver who ended up skating with Dudley, played by Cary Grant, and Julia, played by Loretta Young. But, in that feature the closest they came to each other was when Sylvester drops Julia and the Bishop (David Niven) at the Hamilton mansion.
Joe Rogers works for the Triumphant Insurance Co. while Saunders works for Reliable.