Talk to Bernie, there's one time in his talk menu and then there is a one time choice in his top menu "Talk, Trade, Additional Job, Nothing right now". It's something like "Supplies for camp".
Here's my best recall, you take the task, go see Bernie, talk to him, go back to Jester, end the task, go back to Bernie and choose the Top menu choice, go back to Jester and talk to him about it.
I might got that reversed, but you get the idea. Jester->Task->Bernie->Talk or Choose->Jester->End Task->Bernie->Choose or Talk->Jester->Talk.