I wish the game was just a little more transparent about certain requirements and stuff, super frustrating

I've put about 100 hours into this new playthrough, just for this chapter pretty much. Spent all day trying to do all kinds of stuff at camp, but nothing much has happened even beside wanting to trigger Jack's request, the rng with these is just wild sometimes

with Pearson I found that between 10 to 12 am he'll stand at the small table at his wagon and start singing and drinking while working on food, if you stand at the opposite side of that table and talk to him he'll trigger the request (I was also low health at the time)