Figured it out ! Don't do Pirates Don't Cry right away. After getting two new quests Casqet of Embers and Needle In A Haystack, do Casqet of Embers, then Pirates Don't Cry. Lastly, do Needle In A Haystack (after demonstrating the bomb to Cutter and finding apparatus in cave, teleport to Wandering Wrath, speak with Billy and get challenged to a couple of games of dice.
Apparently, after doing Pirates don't cry, then Needle In A Haystack, enough time has passed for Billy to have visited his new date, which by the way happens to be the brother of the woman Marren!!!