Our advice columnists have heard it all over the years—so we’re diving into the Pay Dirt archives to share classic letters with our readers. Submit your own questions about money here. (It’s anonymous!) 

Dear Pay Dirt,

My parents passed away when my sister and I were teenagers, and we are now both in our late 40s. They left us enough money to finish college plus about $100,000 each. I used those funds very frugally early in life and saved most of it for retirement. My sister burned through everything quickly and has repeatedly gone through boom/bust cycles.

We earn about the same amount, but my family is much more comfortable and has saved a lot more for retirement because of choices we each made. We like to vacation with her family, but inevitably I pay for things in the moment and she either never pays me back or short-changes me. She will also tell me she’s going to send me money for my kids’ birthdays, which I tell them, and then she never pays up—so either they don’t get a gift or I’m on the hook. My husband and I generally do fine, but we are self-employed and are staring down the cost of college for two kids, so we’re careful with our money. We’ll survive if she never pays me back, but it’s a bummer to feel like I’m always on the hook because I’m more careful with my money.
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My sister is sensitive about money and inevitably when I press her to pay me back it’s a bad time for her and I end up feeling terrible. Should I just accept that she’s never going to fully cover her share? I hate nickel-and-diming everything on vacation, but we have a family trip planned to Hawaii, and I simply can’t afford to cover more than my family’s share. How do I change this dynamic?

—Little Sister, Not the Bank

Dear Not the Bank,

I’ll ask this as gently as possible: When is your sister going to ever not be sensitive about money? It sounds like she goes on these trips knowing she can’t pay her share and won’t have to if she plays her cards right. In order to change the dynamic, you need to put some boundaries in place, stat.
From now on, you are no longer in charge of booking accommodations for everyone. If she wants a shared house rather than separate condos, she’ll need to pay for it, and you’ll send her your share. If she does not have money to book her own travel, she does not need to be going on vacation. If she asks why the sudden change, share that you have less cash flow due to upcoming expenses and can no longer spot her. She’ll probably be upset and try to manipulate you, since you’re establishing a new dynamic, but hold your ground.
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Next, spend some time reflecting on why you are enabling her in the first place. Is it guilt for doing so well and being smart with your money? Is it you wanting to look after her due to your parents dying young? We enable people when we have something to gain or lose. Start keeping track of feelings or thoughts you are having when it comes to this situation to see if there is a pattern or trigger. I hope it’ll help you to see your role and find different ways to show support without emptying your pocketbook.

—Elizabeth Spiers

From: My Partner’s Food Addiction Is Breaking Our Budget. (August 23rd 2021).

Please keep questions short (

Dear Pay Dirt,

My spouse intends to leave her half of our house and her savings to her older sisters who constantly take financial advantage of her. She feels sorry for them because they spend every penny on themselves and complain about having no money, so my spouse buys them things, dinners, takes them on vacation without me. One divorced sister makes a six-figure salary, and the other has no children and chooses not to work to serve her husband while shopping and sunbathing almost every day. When she told me of her intentions of not leaving anything to me, her spouse of over 20 years, I was crushed and tried to talk with her, but she becomes furious and ends the conversation. I do not want to leave a single penny to her because she will just give it to her sisters. Would this be wrong?

—I Deserve Better

Ilyce Glink
We Invited Our Friends to Our Beach House. Then They Committed the Ultimate Money Faux Pas.
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Dear I Deserve Better,

Help! I Met Up With My Son-in-Law for “Coffee.” I’m Shocked by What Actually Happened.

My Mom Is Offering Me a Free Place to Stay for College. But There’s a Big Catch.

I Run a Daycare and Agreed to Do My Sister a Simple Favor. What She Did Next Has Ruined My Reputation.

I Thought My Colleague’s Lies Were Harmless. Now He’s Created a Monstrous Rumor Mill.

I think you have to separate your feelings about your spouse and your feelings about her sisters. Your spouse has a right to spend her own money, however deserving you think her sisters may or may not be. But I understand your frustration that you’re not being taken into consideration here. Your wife needs to understand why this feels hurtful to you, and it’s the kind of thing you may want to take up in marital counseling if she’s having trouble talking about it. It seems like there are some trust issues here that transcend the issue of your respective wills and feelings about your sisters-in-law.

(As a side note, I’m a little confused about the fact that your spouse intends to leave half of your house to her sisters, especially if you’re still living there. How would that work?)

That said, I don’t think you can really predict what your wife would do with your money in the event of your passing, and it probably depends on what your financial situations are if that happens. You may think you’re punishing her lazy, good-for-nothing sisters, but you may in fact be punishing your wife, and I doubt it will cause her to regret or reconsider her support for her sisters. So you should make sure you’ve worked out your own motivations and that you’re not just retaliating because you don’t like her plans. I don’t think you want that to be the last thing you leave your wife with if the worst happens.

—E.S.

From: My Husband Is Using Me For Money, But I Don’t Want To Divorce Him. (August 25th, 2021).

More Advice From Slate

My husband and I live in the Pacific Northwest about 3.5 hours from his parents. I always knew his parents were somewhat challenging, but since we relocated slightly closer to them, it has become very clear that my father-in-law is a narcissist. He has been passive-aggressively belittling me for years, but I have coped with it by simply not engaging with him. My husband’s home life when he was young was hard. My father-in-law was verbally and physically abusive, but everyone in the family seems to excuse the behavior as “in the past.”

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