Could Raylan be herded conversationally? Sometimes. Especially if you knew what he wouldn't talk about. There were plenty of social rules he held himself to as well.

"You should. There's plenty of pancakes, Negan helped by cooking the eggs. No meat this morning, but that's because I think if I eat any more bacon this month it's gonna be comin' out of my pores. I plan on goin' up to the Gull later today and getting some different things, fill out our pantry a little bit. Now that I don't have any breakfast places to get a chicken biscuit at."

Oh yeah. Model of health here.