My husband is very out of touch with the whole process of reconciling the checking account. He THINKS he has enough $$, but he doesn't. We spent the first 5 years of marriage with an overdraft protection on our account. Then the next two years we lived in a little tiny town that's bank didn't offer that unless you'd had 6 months without overdraft. IMPOSSIBLE for us. So when we made our next move I suggested (this was not the first time, just the first time he was willing) that we have separate accounts. He works, but I'm the one to pay bills, grocery shop etc. He basically just needs to buy gas. Even that has not been great because he still goes over, so now I just give him cash for two weeks of gas and then he KNOWS what he has and doesn't have. Some people are just not capable of doing things with a checking account, they refuse to learn (or no one has taught them) and they don't get how it works. So they just call the bank to see how much is in their account at the moment, not considering pending items. Now that we use a cash system for him I don't have overdrafts in any accounts.
Here's how it works technically. We have 2 checking accounts, one that I'm the primary on and one that he's the primary on. We have one check card per account - I don't have one for his, or he for mine. However, we both have our names on all accounts, so we can access them if we need to. He doesn't touch mine unless we both agree to it. The checkbook has both our names on it, so he can take a check with him if he's doing an errand for me or something like that.
I also pay all the bills online automatically for the ones that are a set amount, and individually for the others. I get cash out for gas and groceries so I stay in my budget. I also keep a spreadsheet that corresponds to my quicken register, so I can plan for months in advance to know if we can afford something outside of our bills, gas and food money. It works! Takes some time, but honestly having the bills go out automatically saves a ton of time, and thankfully most all of them do that.
Some people overspend because they are careless (like my husband) and others because they are irresponsible or uneducated. I don't know which category your husband fits into. But I would recommend sitting down with a financial planner to go over the best way to budget your money. It is important for people to have discretionary spending money that no one nags you about. It might mean eating out less (and even fast food adds up QUICK) and using that money to just SPEND. But keep it cash, so that you don't go over. Check cards are convenient, but so easy to overdraft with if more then one person is on the account.
Best wishes!