The apartment I rent takes checks still (weird right). The manager usually takes the money out of the bank 1.5-2 weeks after it is due on the first of the month. This was always a nice buffer, in the beginning. We've had our difficulties and struggles to make enough money through changing jobs. I was unemployed for eight months while studying for a new career path and needed a lot of help from my parents. My roommate helped me here and there by buying food, and holding enough money on two occasions until the money was about to come out since my parents weren't always ready to give me rent money (I felt awful asking for money, so I waited usually).

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After this rough time, I scored a very high paying job and spent the next few months catching up as fast as I could. Everything I owed to anyone was paid back. My roommate hated the job he had, and I offered to help out as he switched jobs. That's when the shit started.

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He became very quiet about money in general, and made it extremely weird asking for money for bills, saying shit like "just because you make more money doesn't mean I'm ready to pay for things". I helped him with rent month after month, and added up everything I helped with on a spreadsheet. I knew he was struggling and I wanted to be helpful, but also wanted accountability on his part. Each month, the first would come and go and he wouldn't say a word, no rent money, nothing. I'd have to keep an extra $500 of my money sitting in my account so the checks would go through, and some months I'd have to ask where rent was and he would suddenly come up with excuses why he could only pay a portion. Up and up the money he owed me stacked. Utilities? He didn't bother asking what it was, and didn't pay until I asked. 

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One morning when I woke up to $10 in my bank account, I lost it. He was working, so I texted him a long message about how I expected rent NOW, and how I didn't understand how he never has money even though I'm fully aware of how much money he makes. He pulled the "but I helped you when you needed it" card, like I owed him for it. I shot back with how I paid everything back, and I didn't use help more than a handful of times. Overall I felt justified because month after month I was covering his rent, and not always getting it back in full, or at all. 

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Since this happened, he showed me all his bills and income, and I turned the tables by making him use his account. I subtract utilities from the rent I pay him and it's working well so far. But sometimes I wonder if I was making an ass of myself bitching him out when he was still struggling.