Great post, TheOracle. I replied on Reddit.

I will just comment here that, for the record, I was not offended by the way Halsin was depicted in my playthrough where my Durge romanced Wyll. Halsin made his interest known and was perfectly respectful when declined. At no point did he express judgment of those who want a monogamous relationship; he just said that monogamy wasn't for him. It then never came up again.

Now, for those wanting to romance Halsin specifically, and seeking a monogamous relationship with him, I can understand how not everything I described above would be pleasing. But in my personal experience, I have absolutely no issue with him taking his shot. It seems perfectly fair for him not to make assumptions about the PC's wants and preferences, and even Wyll's for that matter. It must be obvious to the PC that Wyll wants committed monogamy, but I don't see why Halsin should know that. So the aspect of Halsin's approach that seems perfectly fair to me is that he doesn't treat a particular preference as the obvious default.

I did find it interesting that the scene where Halsin makes his overture seems to be timed such that it always happens precisely one long rest before Wyll proposes. At least, that's how it's been in my experience. No matter what other shortcomings there might be, at least Halsin won't wait to make his attempt until after Wyll and the PC have actively committed to spending their lives together.