My guess:

Men define themselves by what they do for a living. The job is an escape mechanism from a world that makes little or no sense otherwise. It's medication.

Then comes the gold watch, the handshake and that "last ride" home. Tomorrow, and forevermore, he can sleep in late and nobody will care. Nobody ever really cared... including Casey.

The music changes everytime the old lover speaks. She never married, never had a family of her own… because she never stopped loving Casey. He used the affair to escape from his life as well and he's carrying the memory of that guilt and regret on top of all the rest.

This, and KK was a Lit major, makes me think of author Robert Ardrey's "Casey." A "real" working man shorn of the song's romanticism (...but based on same &c &c.)


PS: Didja know KK's first language was Tejano Tex-Mex? Shout out to his "Mom" Cantu and all the good folks in McAllen-Brownsville.