Pay Dirt is Slate’s money advice column. Have a question? Send it to Athena and Elizabeth here. (It’s anonymous!)

Dear Pay Dirt,

My grandmother died five years ago. My dad handled all of the estate stuff and the will and whatnot. I inherited a couple of pieces of costume jewelry, and that was it, but I was grieving at the time and didn’t really think much of it. Now I’m starting to wonder if I should’ve inherited more. While talking about a trip I’m planning on taking (and paying for myself), my dad offered to cover my hotel, but I turned him down. He then said something about “Grandma wanted me to give you some money,” which makes me think maybe she did leave me something in her will and my dad, the executor, just kept it for himself.

I’m only 27 and I really don’t know about estates and wills, and I know if I ask my dad, he’ll lie and/or accuse me of being greedy and not caring about my grandma’s death. My dad is very shady about money—he’s incredibly stingy and avoids talking about it (and taught me it was rude to discuss it too). If he were arrested for some sort of financial crime, I would not at all be surprised and would immediately assume he was guilty. I don’t like accepting money or gifts from him for this reason. We have a very distant, cordial relationship, and I don’t want to ruin that. I don’t need the money, but it would be helpful because I’m moving next month. Should I ask him about it or just let it go?

—Bad Dad

Dear Bad Dad,

I don’t think it would hurt to ask, and you should be direct about it. You could open the conversation by mentioning your dad’s offhand comment and saying that if it’s true that your grandmother wanted you to have some money, that it would be incredibly helpful right now because you’re moving. And you can add that if you misunderstood, it’s not a big deal.

That said, I think you should lower your expectations—maybe to sea level—with regard to what the outcome will be. You already know that your dad’s ethics around money are iffy. It sounds like you’re already not hopeful and have established boundaries with him, so this shouldn’t be too hard. And you’re not suggesting that he owes you in this context, so there’s no reason he should resent the conversation.

Dear Pay Dirt,
My youngest son will be 18 in August. He is failing school and constantly lies. He recently quit a job he could walk to from home because he said he wasn’t going to be anyone’s slave. I am frustrated with his not caring and doing whatever he wants, including always getting high. He comes and goes as he pleases, even when he should be in his room attending school. I struggle with my responsibility to him after he turns 18. I’m a single mom approaching retirement soon. I want to take him to the nearest military recruiter and have him sign up. I’m at a loss here. What’s my obligation?

—Totally Frustrated

Dear Totally Frustrated,

I completely understand your frustration. It sounds like your son is having trouble accepting that he has certain responsibilities and doesn’t want to grow up. (Luckily for your son—and the military—you can’t just enlist other people, but he probably does need more structure and discipline.)

You need to talk to him directly about the impending issues and set expectations and boundaries now. It doesn’t sound like he’s going to be ready to fly the coop by August, but you can give him a time frame for starting to achieve some kind of independence. This can include a timeline for having to contribute to rent and expenses if he intends to continue living with you, or a deadline for applying to school (which, in his case, may be something like a shorter program with a vocational school if he hates academic work). Emphasize to him that you cannot afford to subsidize him indefinitely and that nearly everyone has to do work they don’t like to earn money at some point in their lives. But it doesn’t have to be drudgery forever. There are a number of nonprofits that do career counseling for high school students to help them figure out what they want to do, and they often very explicitly focus on people who are disillusioned with school and resistant to the demands of adult life because they just don’t know how to navigate it. Your son’s school can probably recommend some specific resources.

And that may be the case with your son. If he’s struggling at school, he probably doesn’t have very many models of what he’s supposed to do afterward. If his friends are all punting on these questions, it exacerbates the problem because he likely thinks it’s normal. So inasmuch as you can do anything yourself, finding ways to set up structure for him that ease him into these transitions will make it less painful for everyone. If he wants to continue to live under your roof, he needs to come up with a plan for supporting himself within a specified period of time and note that you can help him find resources to do that. And appeal to his desire to do what he wants: If he is supporting himself, he has total freedom and decision-making authority over how he spends his time and money.

Dear Pay Dirt,

My husband works in sales and throughout our 25-year marriage, he has had several bouts of unemployment that usually last about two years. I have had a solid career with no gaps. We have been fortunate to have my steady income and family help during the periods he earns no income.

A few months ago, he found a new job after yet another two years of not working. He makes more than I do now and gets a generous draw and bonus for six months on top of his earnings. For the past two years I have paid for everything and given him money for activities he enjoys without complaint. Because of this, I have been unable to save for a very costly dental procedure that I desperately need. Now that he has a lucrative job with bonus income, I asked that he replenish some of my savings or perhaps take on more bills so I can save. He refuses, stating that I should have been able to save and pay all the bills. He hides all his money in an account that I don’t have access to so he can give it to our adult son, who lays around smoking pot all day. I believe he plans to buy him a new car instead of helping me pay for my dental issues. I am hurt and angry and at a loss. We he wasn’t working my income was “our” money, and now that his is employed again his money is “his.” Nothing I do to appeal to him has worked.

—Beaten-Down Breadwinner

Dear Beaten-Down,

I understand your anger. You’ve subsidized your husband during periods where he struggled, but now that you need help, he’s suggesting it’s entirely your responsibility to deal with it. First, I think you need to underscore to him that you are not asking that he contribute to a luxury slush fund, though you’d be well within your rights to do that, given that you’ve contributed to activities and things he enjoys without complaint. A dental procedure is not a vacation. He is denying you a medical necessity, and he needs to understand that he’s doing that, so he doesn’t view it as just writing you a check for no reason.

These kind of money issues can really erode even good relationships because they destroy trust. You should also talk to him about that. When he needed money, you didn’t second-guess how he spent it and certainly didn’t withhold health care resources. Tell him how hurtful his failure to reciprocate is. Emphasize that this kind of support is a two-way street. And it would be probably be helpful to have these discussions in the context of marriage counseling. These are serious issues, and he can’t just dismiss them, but if he’s already defensive, you probably need a third party to mediate. And you should put it on the table now, because he undergoes another period of unemployment, which could easily happen, and you experience this cycle all over again.

Dear Pay Dirt,

My boyfriend and I have been dating for two years and are discussing marriage. I used to think we were on the same page in most aspects of our financial lives: We both try to live relatively frugally, and our discretionary spending categories are largely aligned. But recently I was browsing Zillow, just for fun, and my boyfriend saw me checking out a home listed for $1.5 million. He asked to see it, and I commented that I’d love to live someplace similar one day. He told me it would be “crazy” for us to pay that much for us for a home. I told him that if he wants to stay in San Francisco, where we live now, and have enough space for a potential family and for him to permanently work from home, we’d probably be lucky to find something suitable for that price (especially since he is very picky about location within the city). He then essentially told me that my standards are “way too high” and that he doesn’t think it is reasonable to spend that much money on housing. (I could not pin him down on exactly what percentage of income he thinks would be “reasonable.”) He then said that he personally would be happy to keep renting forever. I would not be happy renting forever, and I place a lot of importance on having a comfortable home.

Our combined income is about $700,000 (mine is about $300,000 and his is $400,000) and our combined savings is about $400,000 (not counting retirement savings, which is fairly substantial as well). We don’t have significant debt or other financial responsibilities, so it seems clear to me that we could afford this, if we wanted to. Am I wrong in thinking that we could afford a house in this price range? I’ve never owned property before, so maybe I’m not accounting for some costs, but based on my math this seems doable. And how do we reconcile our different views on this? I haven’t yet revisited this conversation with him, and I don’t know how to begin to talk to him about this in a productive way.

—Hoping for a Home

Dear Hoping,

I think you’re definitely on track to be able to afford that, especially if your credit is good. Your boyfriend may not understand the ins and outs of mortgage financing, and depending on what you’re paying for a rental, your mortgage payments may end up being less than rent. So I think it’s worth taking your boyfriend to talk to a lender just to walk through the process. His objection seems to be that he doesn’t want to spend a lot of money on housing, but depending on your specifics, owning may actually be cheaper than renting, so frame it as a potentially cost-effective proposition.

But this may be a premature discussion since you haven’t made any permanent commitments to each other yet. (This wouldn’t have to be marriage, but jointly owning a home isn’t something you should do without some understanding that it’s not a temporary thing.) It’s also a little unclear from your letter whether you’re co-habitating now. A lot of people don’t really need or want more physical space until they have kids or have been together a long time in the same space or work from home together. Your boyfriend’s feeling about how much space he needs may change over the course of your relationship (especially if kids enter the picture). So I wouldn’t consider this a permanent state of being, especially if you’re in your 20s.

It may also be the case that your boyfriend is reluctant to talk about owning because it represents a kind of permanence, and he may not want to stay in San Francisco forever. And renting doesn’t preclude having a comfortable home. So this is really about teasing out his underlying objections and also what ownership means to you. But I don’t think it’s unreasonable for you to ask him to explore the possibility from a place of really understanding the pros and cons.


Classic Prudie

A few months ago, I discovered I was pregnant. I’m only 20, and my husband is as well; we lived with his parents at the time. We decided on adoption, but his family would not accept that option and began to blame me for “making my husband reject his child.” We’ve been pretending we’re keeping the baby to keep the peace and moved out of state to get away from everything. My husband insists on telling his parents that the baby was a stillborn or died during delivery. I’m not sure what the right thing to do is.