His face is a journey as he takes that information in. He knew about Raylan's.... dalliances with Doc, he'd heard it straight from the cowboy's own mouth on the porch of 1308 not so long ago. Had even given him some proper advice about how loving more than on person can, but won't always, work.

This sounds like the exact opposite of what he'd told Raylan.

"...Tim? When did this triangle become a square?" What in the name of Satan and all that's Holy did he miss?!