I only noticed it in the last version 7B, though I've only tested it in that version and 8. Also it was specifically drunk inmates that wouldn't ask you to drink. Sober inmates would still ask.That hasn't been my experience. They've always asked Karryn to drink, no matter what her clothes are like. Of course they ask more when she's fully exposed since asking her to flash isn't an option anymore.
It was honestly a neat little mechanic to discover, since in that version mind recovered slower when you denied drinks. So if the entire table was drunk you could "allow drinks" while there to recover more mind. But with the way mind currently works it'd just make the bar job easier.