I was living with 4 of my fraternity brothers for several years in college. I would pay the utilities then collect the amount owed from each roomate every 2 months or so. Well come the end of our lease I procrastinated so much that I didn't calculate the final utilities until one of my roommates moved out.

Let me give you some background on this guy. He was on student loans all through college going to a private university(35k a year) working part time on and off and is now taking student loans to go to law school.

The total came to ~400$. Now this is higher than usual(I procrastinated an extra 2 months to add it all up) so there was no way in hell I was going to be able to get that from him all at once given that he doesn't even have a part-time job now. I rationalized to myself that I would wait until he finished law school and got a job to ask him for the money so it wouldn't be such a shock to his limited budget.

Honestly if it was like 100$ I would just let it slide, but 400$ is quite a bit of money. Should I consider it gone or is it still kosher to bring it up?