He’s horrible with money

Lots of money letters lately.

This guy's other woman: Sallie Mae.

Dear Meredith,

I have recently moved in with my boyfriend, "Dan." We are both in our mid-20s and I would say our relationship is good overall. I have loved Dan a long time, and I know he feels the same about me. Lately, however, I have become increasingly stressed about one thing: his finances.

Let me start by saying that in terms of joint bills (rent, utilities, etc.) Dan contributes 50 percent and has never asked to borrow money from me. He was unemployed for a while, but has had a job for about a year now and works very hard. My concern is that he's lackadaisical about his personal financial situation -- things like debt, student loan payments, and credit rating. While I always knew he was more "relaxed" about these things than I am, I became more aware of the situation when we applied for our apartment. He mentioned that his credit score is bad. We still got the apartment, but since then I have become more stressed by the issue.

Dan tells me that he doesn't exactly know how much debt from multiple student loan lenders he has, or even what his monthly payments are. He tries to pay when he can, but doesn't seem to make it a priority. I know that he is really behind on payments. While I have my share of loan debt as well, I can't imagine having this kind of attitude about it. Dan says he thinks collectors are calling him, but that he avoids ever listening to their messages. I wish he would at least take control. I've tried explaining to him how his bad credit score could impact the future, but lately it only makes him mad. He says it is his problem to sort out, not mine. Even when he did his taxes he said he "never got his tax return," which confuses me, especially if he never followed up. Furthermore, while he does help pay our joint bills, I have to do all the basic bill management.

Dan and I have talked openly about how differently we relate to money. As the daughter of a small business owner, I have always prided myself on being excellent at managing my money. I worked hard to help put myself through school, and was able to accumulate a good amount of savings in the years after graduation. This kind of financial security and independence is important to me. Dan, on the other hand, came from a very different background, was pretty poor growing up, and acknowledges that his family has never really known or taught him how to handle money. He will give $20 to homeless people, which I want to consider a generous act, but instead end up feeling stressed that he is giving money away instead of sorting out his own problems. He will go out for dinners with coworkers and friends that I feel he probably can't afford while I am trying to save every penny.

I have told Dan that the reason I want to help him get his finances in order is because it could impact both of our futures if we want to someday own a home (which is important to me). I've suggested maybe we find a third party, like a financial adviser who could help him. He is not open to these things, says he will sort it out, but then continues to do nothing.

So, my basic question: as a live-in girlfriend, how involved should I be? Should I continue to ask him to deal with his financial problems or just accept the fact that it truly is his problem? Is his attitude a deal-breaker? Are we just too different?

– For love or money, Boston

FLOM, Dan is scared to find out how much he owes. I don't blame him. I'm scared for Dan.

And yes, the tax thing is a bit weird. Sounds like he never filed his taxes, but that's just a guess.
His financial problems don't make this a deal-breaker. Frankly, in most working partnerships/marriages, one person takes on the responsibility of money management. And I know of many relationships where one partner has helped the other get out of debt simply by getting them on a schedule. And he's in his 20s. Yes, that's relevant. He hasn't learned how to do this yet, but he's not hopeless.

The question is -- will he ever let you help?

The trick is to let Dan know that you're not going to judge him or make him feel small if he reveals his ugly numbers. Tell him that you have debt, too, and that there are aspects of your life that parallel his money disorganization. Maybe you're bad about car repairs or calling relatives. Maybe his social skills are better. In partnerships, we have to respect our significant other's skills. You're good with money. He brings other talents to the table.

It's only a deal-breaker if he continues to refuse to let you help. But my guess is that if you tell him -- while smiling -- that sitting down with his bills (and a tub of ice cream and maybe two glasses of wine) is going to be a friendly and loving process, and that it won't be about disciplining him, I think he'll give in.

I like that Dan is self-aware about his inability to manage anything financial. At least he's not pretending to be good at it. And I think it's incredibly important that he has never asked for money, that he's not someone who's looking to burden you or freeload. But Dan does have to prove that he can get personal. Financial intimacy is pretty big. In Dan's case, financial intimacy is like .... running around naked in the daylight after weeks of not washing or shaving.
But he's not the only one who'll be running around naked in this relationship. Remind him that eventually, you will need his skills to help straighten out something embarrassing in your life. You'll want to be able to lean on him for that. How can you be vulnerable about your weaknesses when he won't show you his?

See if he responds to that approach. If he doesn't, yes, you're allowed to worry. And remember -- even if he learns how to pay bills, he's never going to adopt your spending habits. You can ask him to be responsible, but you can't ask him to do everything you want him to do with his wallet.
Everyone? I've always thought that financial messes make fine partners as long as they give up control and let their significant others help them. Am I right? Is it relevant that Dan contributes 50 percent or is the letter writer setting herself up for a life of debt? At what point should partners reveal their numbers? Thoughts on how to talk about this? Discuss.

– Meredith