A dating quest (Unless somehow you can date an NPC.), I fear, would cause more drama than it is worth in the long run.
The PK thing doesn't sound too bad of an idea, just make sure you have everyone's permission. (I think you covered that, though.)
So, I'd have to say no to the dating and yes to the PK, it would kind of be a Wall of Fame almost.
Oh, by the way, there IS a patch out there that makes the females naked, not the males for some strange reason. I don't remember its name, this was when I was playing PWI and someone sort of "leaked" the code, next thing we know, we have a whole thread about it that was removed 2 or so hours later and a warning: "If you do this again, you will be permanently be banned to both the game and forums." And, yes, I know about the waterfalls in Valley of Disaster, awkward and funny at the same time.
