They probably can't get to the bottom of the Raylan and Doc situation simply because Doc believes there is no situation. Raylan's never mentioned otherwise and Doc has more closets to sequester his thoughts and feelings than any nomadic man ought to be carrying around with him.

Doc had also never believed that there was any space for Malcolm in Raylan's world. He had said as much. He thinks it a little irresponsible if Raylan had led him to believe otherwise, but he suspects it might not have been intentional or deliberately manipulative. Raylan is just... stupid that way.

"Oh, Malcolm," Doc says with a small, quiet sigh. "There is no going back. There was never any going back the moment you met him. You will never be able to look at him without feeling anything. The only way is forward."