Flint listens quietly, taking it all in, watching the pain twist in Raylan's features. He notes the bottle that doesn't empty, quirking a brow and setting his bottle aside in favor of sharing that bottle of unending whiskey if Raylan wanted to.

As for Tim, there is a little flicker of confusion, he didn't meet Tim on the barge. But their Theater Professor, sure, he knew him well enough from that Alternate world they shared. He wracks his brain around it a little, surprised that that is the sort he'd go for, but then remembering how vastly different they all were. Now he wonders what Tim was really like.

"I'm sorry, for what it's worth." Which he knows isn't a whole lot but it's generally what people say when you lose someone.

"He was a Warden, right?" Just a shot in the dark if they worked together.

"So you'll see him again when you go back? And your ex-wife? She's alive? Surely there's some solace in that. Those people you love may not be here with you but it's something you have to go back to." He doesn't say it, he doesn't want to taint the positive, but he doesn't have any of that to go back to.

"What was your deal with the Admiral?"