However, I DO have a problem if he does have money but just spends all of it on dumb shit he can't really afford. He'll show off his new extravagant purchase then in the same breath lament that he's all "tapped out" and can't afford to grab a slice of pizza for dinner.
It's like he has no self-control when it comes to buying toys. When he can't pay his rent but he's bragging about his new Xbox, shit ain't right. When he can't afford to go on a quick getaway with me for the weekend, but can buy yet ANOTHER monitor for his computer, it makes me get those squiggly lines of frustration like I'm an angry cartoon.
I don't care what he does with his money, but it affects me because he's needlessly broke all the time. At first, I'll try to accommodate it and suggest we go on some low-cost dates but there are only so many times I can eat take out from Taco Bell then sit in a park. Somehow I'll end up paying for us to go to nicer places (which he can't afford because he just upgraded his iPhone so he's broke until his next paycheck.)
He doesn't need to have an Excel spreadsheet with all of his purchases for the month, but a little money management would go a long way. That's all I'm saying.