Josh will do his job. He will be polite and act understanding. But I know Jews. They look at people who are foolish or careless with money like carnival freaks. Curiosities.
"How could you not have known you were potentially liable for his lawyer's fees? Why didn't you work out a repayment plan as soon as the ruling was made? How could you have let the debt snowball like this? Do you have active income coming in monthly? Why did you go on vacation? Wait, more than once?"
These are some of the questions that will be pinging around Josh's head while he acts like a sympathetic buddy to these two enormous (in every way) fuck ups.