Pay Dirt

I Just Found Out My Incredibly Cheap Friend Is Heir to a Massive Fortune

Introducing Pay Dirt, Slate’s new money advice column.

Man's torso, with his hand pulling at his empty pocket
Photo illustration by Slate. Photos by Getty Images Plus and Spoon Graphics.

Pay Dirt is Slate’s new advice column examining money and relationships. Every week, columnists Elizabeth Spiers and Athena Valentine will tackle your thorny financial questions. Look for Athena’s debut column on Saturday. Have a money question? Send it to Athena and Elizabeth here. (It’s anonymous!)

Dear Pay Dirt,

I have a friend who’s always been a little cheap with shared checks. If I throw my card down for ease and let people Venmo me, he’ll pay me, like, a conservative estimate of his portion (often short of the real total) and also not take tax or tip into account. I always kind of forget about this until he does it again. A few months ago, he estimated $25 when he owed me $40, and I was like, “Bro,” and he seemed perplexed and gave me the $40. I tell you all this because on our last hangout, it was just us, and through other conversation about COVID and his current joblessness, he reluctantly revealed he is an heir to one of the biggest family fortunes in America. He has virtually endless funds for the rest of his life. I had zero idea. I don’t think many people who know him do. His family seemed normal (they have a different last name than the famous one). I don’t really know how to react to this, especially in light of just thinking I had a pretty cheap friend. Instead, I was partly subsidizing an extremely rich person! What do you think is going on in this person’s brain? Do you think I should point out to him that he does this explicitly?

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—Rich People, Man

Dear Rich People, Man,

I think there are several possibilities here. One is that your friend is simply very bad at math. Fortunately, for you, Venmo has a function designed explicitly for managing the mathematically inept: You can request payment directly, in the amount that you choose. Then there’s no confusion about who owes what, and if he’s intentionally underpaying you, he’ll have to admit it and make a case for why.

Another possibility is that your friend has family money coming but is not benefiting from it at the moment. I say this, having bought many a $3 happy hour beer for underemployed friends in my 20s who had trust funds but couldn’t access them yet and whose parents did not subsidize them in the hopes that they would learn to be independent. I was not obligated to do that, and neither are you, but it could explain why your friend appears to be pinching his pennies.

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In both of these cases, your friend is oblivious and possibly cash-poor, but not a cheap jerk. But I’ve also known a few rich people who really are cheap jerks, and are convinced that this quality is part of the reason why they stay rich. If your friend fits into that category, the lack of generosity would probably be apparent in other areas, too, and I think it would be reasonable to confront him about it the next time it comes up. Note that you don’t mind picking up more of the check occasionally, but it’s not fair to you that this keeps happening.

Dear Pay Dirt,

My brother was murdered in a robbery when my niece “Jo” was 16. The case is still open. Her mother is worthless, so Jo came to live with me through the last years of high school and through college. She is the closest I will ever have to a child of my own.  When Jo got engaged, I paid for the wedding, the honeymoon, and the down payment for a house. It might seem extravagant, but I made very, very good money at the time. I am retired now.

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My other niece, “Em,” has gotten engaged and has “expectations” that her parents will not be able to fulfill. Their jobs don’t pay well, and they have two other children in college. Em and her fiancé have creative careers and no savings. Apparently I entered into an unwitting family contract where I am obligated to equally spend on Em what I did Jo. Em and her fiancé actually made this argument to me. Em told me it wasn’t “fair” otherwise. I told Em I would pay for her to see a therapist or a priest because there was something wrong with her soul. She might be several years younger than Jo but is an educated adult woman, and envying her orphan cousin is morally repugnant. Em got offended and went crying to the rest of the family. Most of them are mortified, but my brother-in-law has always been wrapped around Em’s little finger. He argued with me, and I told him to take a loan out if his baby’s dream wedding is worth it. He has cut off contact with me and the rest of my family. My sister has sent me one text with the word “Sorry.” She has always followed her husband’s lead during their marriage. Her other children have been instructed to not talk to me. This discord wounds me—my sister and I lost our parents young, another sibling to suicide, and then our brother. We have extended family, but tragedy holds tight. Jo has been having anxiety attacks over all this drama, and part of me hates Em for putting us all through this. What can I do?

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—Wedded Expectations

Dear Wedded Expectations,

The only person who’s not being fair here is Em, and it sounds like her father is enabling her unreasonable expectations. What you did for Jo was an extraordinary act of generosity, not an endowment program for soon-to-be-married nieces. It’s unfortunate that Em has so little empathy for her cousin’s situation and cannot differentiate between Jo’s challenges and her own. But I would avoid insulting your niece’s character, however inflated her sense of entitlement. It will be punctured by the realities of life and working in a creative field soon enough, and if you value your relationship with your sister, you want to leave everyone room to eventually get past this and mend things.

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But you should also make it clear to your brother-in-law, who should know better, that what you do with your money is your decision alone, and that he and your sister are actually Em’s parents. If they want her to have an expensive wedding, traditional etiquette says they should pay for it. It’s not your responsibility to fill gaps that they can’t or won’t.

Dear Pay Dirt,

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A couple years ago, I was in a terrible car accident that was caused by negligence on the part of the other driver. At the end of last year, I finally got my settlement. I got much, much more than I had expected to get at the beginning of the process. I am currently doing well, but my doctor has said that down the road I could possibly need more treatment or surgeries. Some of these issues could be quite expensive and could impede my ability to work. I sat down with a financial adviser to go over possible outcomes, and he gave me a very conservative estimate of how much I should save.

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The problem is that I’m holding on to about three times that amount. I always thought that if I ever got ahold of this kind of money, I’d give most of it away. I’ve given a lot of it away, but I keep feeling bad about how much I’m keeping. Throughout my life, I’ve worked on and off to support causes related to economic justice. Most of my friends feel the same way, and my family who doesn’t is basically mocking me because I’m not standing behind my principles. After they said this, I was too afraid to tell my friends. I feel like a fraud. I had all these wonderful, idealistic goals in the abstract, but when the chips were down, I abandoned them. I know there are so many people suffering right now, but I’m so afraid of something happening to me and not having the resources to get through it. Should I just get over this and let go of the extra money?

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—Stingy Savings

Dear Stingy Savings,

No one really knows what they’d do with a big, unexpected pile of money until it’s handed to them. Humans are terrible at predicting our own future behavior because our predictions tend to reflect our good intentions more than our likely courses of action. This is why every Jan. 1, millions of Americans insist they will spend the next year eating better, exercising more, studying Mandarin—and end up making exactly the same resolutions 12 months later.

That said, I believe you are being far too hard on yourself, and the fact that your family is mocking you for what they perceive as imperfect generosity when they have no intention of being charitable themselves reflects badly on them, not you. You don’t have to give every last bit of your money away to support causes you care about, and it doesn’t make you a hypocrite to write a smaller check. You legitimately have some potential medical expenses coming up, and the settlement is designed to help you cover that. Setting aside money for your own future isn’t just reasonable, it’s the responsible thing to do. Calculate what you think you might need in a worst-case situation, and consider the balance something you can spend flexibly on other things, like charitable giving. You already mentioned that you’re working with a financial planner, so they should be able to help you figure out a system of giving that allows you to fund the things you care about while also keeping your savings intact. If consistency is important to you, it will ensure that your funds are being put to work in the way that you want over time.

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Dear Pay Dirt,

My roommate and I split utilities equally. I’m the one who set up the accounts, so I pay each month and then just tell her how much she owes me. For a few months a couple of years ago, I was really stressed out and struggling with some undiagnosed mental health stuff, and I just couldn’t bring myself to tally how much she owed me and ask for her half. I still paid the bills, and she never asked me for how much she owed. Is there any way to ask for her half of those bills now? Or should I just consider it a gift now that so much time has passed? It’s not like I’m on the verge of financial ruin unless I get that money, but it’s probably a couple hundred dollars. The idea of asking at this point fills me with dread.

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—Late Fees

Dear Late Fees,

I would feel differently about your dilemma if you had covered a couple hundred dollars’ worth of utilities last month and not “a couple of years ago.” I think there’s a statute of limitations on smaller amounts that, by your own admission, you don’t desperately need. I would also feel differently if we were talking about a much larger sum of money—a four- or five-figure loan, for example. It’s still your right to ask, but it would probably create more resentment than it’s worth.

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You also state that talking to your roommate about this fills you with dread, so think about it this way: Would you be willing to absorb that couple hundred dollars to avoid the stress of a potential confrontation? If the answer is yes, you’d be making a rational decision to let it go. The money would not be worth it.

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But I also think you should examine why this is still bothering you, so much later. Are you hurt that she didn’t realize you were doing this, or didn’t ask, or was just oblivious to what you were struggling with at the time? If that’s what’s really making you feel like she owes a debt that hasn’t been reconciled, it’s probably worth talking to her about it. Because it’s not really about the money.

—Elizabeth

Classic Prudie

Four years ago my mother-in-law had a stroke and lost the use of her right arm. She felt that she couldn’t use much of her jewelry anymore so she gave me a few of her pieces. Although the gesture was sweet, the jewelry was not my taste. I had kept it put away for many years, but finally this past winter, money was a little tight and I decided to sell some of my least favorite. I ended up using the money for groceries so we could have a little extra money for Christmas and a birthday for our youngest child. Just a month or so ago my mother-in-law called me up to asked if she could borrow for the very hoop earrings I sold and my heart sank! I told her the clasp was broken from a one time use and were unusable, and she left it at that. Then a couple of weeks ago she asked my husband if he remembered the heart necklace she gave me, he told her he did, she also asked for that back so she could wear it again. Well, I sold that one too! My husband has no idea I sold these items and I don’t think he would say anything about it if I told him. Now I’m hoping she doesn’t ask for it again, but I know she will. Do I fess up? 

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