Sort of to add onto this, which I think does advance this to possible dialogue tree bugs:
Shadowheart:
She has now confessed in detail her desire to be a Dark Justiciar twice; once because of what I believe is approval, and a second time because Halsin mentioned them.
Halsin:
I *specifically* avoided anything that had even a hint of “romance” in the dialogue at the party at night, and in the morning I have the option to apologize to him for coming on too hard?! This has got to be an incorrectly tripped flag.