You should always pay people the money you owe them
Will owes his friend a grand total of 1,700 dollars.
Will wants to decide if he should bring it up to his friend.
Will decides to bring it up himself so that he can bring it up at a time in his life when paying it back would not hurt him.
Will stays quiet and hopes that either his friend won't bring it up or will get the amount wrong.
Will pays his friend back all the money he owes him.
Unfortunately his friend brings it up at a time when Will has very little money to get by.