Mustachians! I need your help!
I am at my wit's end and don't know what to do in this situation.
I am the one in control of our marriage finances. All income goes into the central checking account and gets disbursed to the budget with YNAB (You Need a Budget). My husband agrees that I do a better job controlling the money, and goes along with the budget pretty well. We both also have separate accounts with personal money. These are funded with our monthly allowance of $100/month and are used for anything we want, gifts for each other, and things not covered in the budget (clothes, haircuts mostly). Previous to using YNAB, I still controlled all the finances and paid off his credit card debt (a couple thousand dollars) that he had amassed before we got married. After paying off his credit card, I gave it back to him, saying it is his responsibility now to use it and pay it off monthly. HOWEVER...
Last year I found out he still had debt owed to Paypal. He had racked up about $700 in debt, mainly by giving money to his adult daughter. When I found out, I gave him all the money that was supposed to go to savings (and my allowance) to pay off this debt. I was angry, and he was upset I was not giving myself my allowance, but I could do without it. I just didn't want anymore debt.
Fast forward to this month. He accidentally uses the wrong CC to pay for a personal item. I ask him to just forward some money from his account to the joint account to pay for the expense. He doesn't have the money in his account, and was planning on using the credit card float until he got his allowance in September (around the 20th).
When I asked him why he bought this item that he knew he didn't have the money for, he just said, "I'm not like you." I don't understand why he continues to spend money he doesn't have. We do pretty well, and any overspends in our budget can be covered from other categories. But, I don't see his personal accounts. I can't cover overspends I don't see, and he doesn't tell me about them because he's embarrassed and doesn't want to disappoint me.
I learned, at the same time I learned about his paypal debt, that he pays a monthly fee for his personal checking account. I couldn't believe it. I haven't paid for a checking account since I was in college! He said he could make it a free account, but I'm sure he hasn't done that yet (almost a year later). So, already $12 of his $100 allowance is gone every month.
I used to have budget meetings, but he would always say, "Whatever you want to do, do that." So, I stopped having budget meetings, because he wasn't giving any input. I don't know how to bring this subject up to him because he will either get defensive and angry, or he will (more likely) get sad and depressed and mopey and not say anything. Add to the fact that I have social anxiety and don't have confidence in my ability to express myself clearly (especially in such an anxiety-ridden subject), and we have a big problem. What can I do? I thought about giving him a bigger allowance, and me a smaller one, but frankly, I don't think that will solve the problem of him spending money he doesn't have. He will just expand how much he buys to overspend again.
TL;DR
My husband gets $100/month in allowance that he is free to spend anyway he wants, but can't stay in budget with this money. I am anxious to talk to him about it because he feels very sensitive and hopeless on the subject. What can I do, if anything, to get him to understand that he should not spend more than he has?