My boyfriend is bad with money

 Dear Cary,

I'm a lady who has it pretty good -- a place to live, food to eat, a full-time job and a lovely boyfriend with whom I cohabit. For the most part, I'm very happy. I make most bills on time and live with only a mildly stressful debt load -- pretty good for one's early/mid-20s.

My issue is with said lovely boyfriend. He's incredibly bad with money. He never paid his electricity bills at his old apartment and so he had his power cut off at least once every three months. His cellphone would constantly be cut off too. I would raise eyebrows at that since it was a big warning sign, but he waved me off with, "It's my problem, not yours." Then I discovered that he's not filed his taxes in almost five years, even though he likely would've been entitled to a substantial refund each time. I pestered him for an entire month prior to the submission deadline to file all his back taxes so that he might pay off some of the debt he's accumulated, which he never did. He tried desperately to e-file the night before but of course the servers were overloaded and he missed out. For another year. I had to find and secure a rental apartment in my name. Utility bills are in my name. I buy almost all of the groceries because otherwise we would subsist on ramen, tofu and maybe a mustard packet. He pays me the half he owes, but only after repeated requests for money, which I loathe making. It makes me feel like a shrieking harpy to constantly be on him like this but I'm really concerned.

I realize that a lot of this stuff is fairly standard for our age group but it really worries me. Were he not a mind-blowingly incredible person in every other way (he's brilliantly smart, emotionally intelligent, creative, talented and for the most part very thoughtful), I would split -- I'm terrified of potentially marrying someone who could destroy my financial welfare. I don't think he avoids money-related things on purpose, though I know they aren't pleasant to dwell on. I honestly think that it never even occurs to him until creditors are calling every 10 minutes (or he doesn't get the call because he didn't pay his damn phone bill). He's just absolutely flippin' clueless about due dates and fiscal responsibility.

We communicate so well about everything else but I don't know how to adequately get the importance of this issue across to him. He gets very upset if I mention his lack of luck in finding a job or if I start audibly stressing about our situation. The good stuff in our relationship is good enough that it's not enough to make me think of leaving now, but in four or five years? When we're thinking about houses and babies? I need to be with someone who can tell his arse from an audit.

My question is this: How can I convince him that his financial state is potentially a huge problem in the future if he doesn't shape up? What kind of resources can I direct him to to get his shit together? I know every letter you're getting lately is probably along the same lines, but I hope you might have some sort of wisdom for me that is gained by being ... you know ... not 24 anymore.

Scrooge McBitch

Dear Scrooge McBitch,

You're not a scrooge. You're a person whose economic well-being is threatened by someone else's financial immaturity. As long as you're living together, it's not just his problem. It's your problem.

I favor doing something pretty drastic. I suggest you sever him from all your financial transactions and have him move out.

Wow. That sounds pretty drastic. But you don't have to break up. You could still have a relationship. Just sever your finances. After all, if he doesn't think money is important, then he shouldn't mind. Be his girlfriend. Just don't have anything to do with him financially. Go cold-turkey. Date, sleep together, eat meals together and all the other fun things. Just keep all your finances completely separate. Do not incur any joint debts. Do not enter into any joint financial agreements.

During this period of time, he has a choice. He can endeavor to acquire realistic economic behaviors. He can take courses. He can study books. He can get counseling. He can start a business. He can begin recording his daily expenditures and income. He can talk to the IRS and set up a payment program.

Or he can do nothing.

And you can watch from a safe distance.

Let's be clear: His behavior is extreme. Repeated cutoffs of the utilities is extreme. Years of not filing taxes is extreme. If he won't admit that, then either he doesn't see it, in which case his awareness is distorted, or more likely, he does see it, and it just scares the living crap out of him. (And he does the typical guy thing of completely ignoring it.)

Here is the operative truth in your situation: We do not change until what we are doing stops working. Change sucks. So we do not change until we have to. We'll do anything to avoid change. We'll lie. We'll get angry. We'll do whatever we have to.

We do not change until our system stops working. His system is still working.

You can't make people change. But when you set up firm boundaries, you accomplish two things. One, you protect yourself. And two, you communicate something. That doesn't mean he'll change. That's up to him. But your action can be a catalyst for change.

So if you are serious about making a life with him, it might not be such a bad gamble: Tell him to move out and get his finances together. Tell him you love him and would like to have a future with him but only on these terms, and just watch from the safety of the sidelines.

We're almost done here. But I would like to wonder aloud, just briefly, in case you, as a woman, are curious, exactly what cultural bias it is that makes his sort of financial immaturity less shameful than, say, sexual immaturity, or not being able to tie your shoes or comb your hair, or having a learning disability. I wonder what role social class plays in it. I wonder what role male privilege plays in it. Because, if you look at it from the angle of male and female social roles, he's really getting a pretty good deal from you. And maybe it has something to do, too, with the knowledge a white male has that, any time he wants to, he can clean up his act and go out and earn more than you do. Maybe a certain privilege, built into the system, rewards him for, and insulates him from, his own irresponsibility.

I'm not saying I know this for a fact. I haven't studied it. I'm no sociologist or economist or political scientist. I'm just wondering aloud. I just know that I'm a white male and I've always been able to kind of slide for long periods and then buckle down in a pinch. There's always been a kind of safety net. (I've also broken into my own house a few times and nobody ever called the cops on me.)

OK, one other thing: Once I started a business, I found money to be extremely interesting. Following money to see where it goes when you're sleeping is interesting. Numbers are interesting. You can feel sort of helpless if you believe that you only have X amount of monthly dollars to work with. But when money starts to flow through your account in larger amounts, you start to get creative. Thinking about revenue is more interesting than thinking about bills. Revenue is creative.

So, while some might say that the last thing you want an economically immature person to do is start a business, it might actually help him. It might give him a reason to count his money.

What? You want more advice?

• Read more Cary Tennis in the Since You Asked directory.
• See what others are saying and/or join the conversation in the Table Talk forum.
• Ask for advice. Letter writers: Please think carefully! By sending a letter to advice@salon.com, you are giving Salon permission to publish it. Once you submit it, it may not be possible to rescind it. So be sure. If you are not sure, sleep on it. You can always send tomorrow. Ready? OK, Submit your letter for publication.
• Or, just make a comment to Cary Tennis not for publication.
• Or, send a letter to Salon's editors not for publication.