The quest "Reassuring the Masses" concludes with us talking to Katliss; Glynard joins the conversation and, near the end, mentions that if we're passing by the Wandering Stairs there's "a regular who's eager to meet you".

This appears to be intended to point us towards the role quests if we haven't done them yet, but as far as I have seen, this same dialogue is used even if you are partway through or have fully completed a quest chain already.

Is this an error? Should it be triggering different comments depending on your progress in the various role quests?

It's quite confusing to be told that there's someone who wants to "meet" us when we're already underway with the quests. Some of the questgivers aren't even at the bar in the later parts of their quest chains.

If you do make a detour down to the bar on Glynard's apparent instructions, you'll find that there is nobody new for you to meet, and if you talk to Glynard he makes no further mention of this person and doesn't say anything about continuing to help the existing patrons either. So it seems like a dead end and doesn't have the intended effect of reminding you to finish the quest chain.