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

Dear Pay Dirt,

I am hoping you can settle an ongoing disagreement that I am having with my father. I am 30 and live with my dad in medium-sized city. My parents split up when I was in high school, and he moved here when I went to college across the country. After I graduated, I stayed in my college town for several years. Now I’ve relocated for a job in his city. He invited me to live with him for a year (or more!) to save some money and get settled, and it’s been great for our relationship so far. We have a weekly movie night together, and he encourages me to invite new friends over for meals, it’s really nice. But four months in, we have one frequent disagreement about money that I need help with.

My dad thinks of everything in terms of the annual cost, a classic kind of Boomer “daily Starbucks and avocado toast” catastrophizing. I don’t think about money this way at all. I look at my income and expenses each month and think about whether I can afford things based on that. I learned, from both my parents early on, to pay myself first, so I do save, but I also spend money on things that make my life better.

My dad disagrees with many of these expenditures and shares his disapproval basically whenever he wants. He gets upset at the way I’m spending my money, despite the fact that it’s my money! For example, he hates that I pay for music streaming. He thinks I should take that “$300 per year” and “invest” in physical music that I can then upload digitally. I have explained that streaming works for my lifestyle and how I listen to music, and he just shakes his head. He does this with the granola I prefer (“$10 a bag! That’s $520 per year!”), the organic produce I opt for (“You’re doubling, tripling your annual food expenditure, and for what!?”), and the cleaner I spend $150 on each month (“$2,000 a year not to scrub your own toilet, it’s madness”).

I just fundamentally see these things differently. The cleaner, for example, allows me to feel comfortable in the house knowing that I only have to do rudimentary cleaning because a deep clean is happening each month. (My dad probably deep cleaned the house once a year, before.) I have made all of these arguments to my dad but he still thinks I’m basically throwing money away all the time. The worst part is, when he is very mad about something, he will say, well if you can afford gourmet ice cream (or whatever) maybe you can afford to pay me more to live here. This is very confusing to me. I told him from the beginning I would pay whatever he thought was fair. He owns his house outright, but of course there are taxes (high in our area) and utilities, etc. He said early on that $200 a month for shared utilities was “more than enough,” and so that is what I give him each month.

And everything is fine until he gets all boomery about buying me buying a new-release hardback book instead of waiting to buy it used or waiting for a sale on Kindle or whatever. I do like living with my dad most of the time, but these arguments are getting so tiring. Any advice?

—Actually I’m Good With Money, Thanks

Dear Actually I’m Good With Money, Thanks,

Let’s agree your dad’s delivery is terrible, but recognize he might have a point buried under all that math.

You’re paying $200/month to live in a medium-sized city. Average market rate in a medium-sized city is probably $1,200 to $1,500 minimum for a studio or one-bedroom apartment. That means you’re getting a $1,000+ monthly subsidy from your father. Which means you’re not actually “good with money”—you’re good with his money. The lifestyle you’re living (house cleaner, organic everything, hardback books) is only possible because your housing costs are artificially low.

Your dad sees you spending freely on discretionary items while he’s subsidizing your rent to the tune of $12,000+ per year. From his perspective, you’re treating his generosity like it’s invisible. That would frustrate anyone.

Now, does that give him the right to threaten rent increases when he’s mad about your ice cream? No. That’s manipulative and needs to stop. But before you dig in about boundaries, you need to recognize what’s actually happening here: You’re living a lifestyle you may not be able to afford on your own salary, and your father is watching you act like you earned it yourself.
His concern probably isn’t about control—it’s about whether you understand that this situation is temporary. When you move out and pay real rent, will you still be able to afford the $150/month cleaner? The premium granola? He’s worried you don’t have a realistic picture of your actual financial position.

You might want to sit down and actually calculate what you could afford if you were paying market rent. Be honest with yourself about what would have to change. Then have a conversation with your dad that acknowledges his generosity: “I realize I’m able to live the way I do because you’re charging me so little. I appreciate that more than I’ve probably shown. But the comments about my spending feel controlling. If you think $200 isn’t enough, let’s talk about a fair number. If it is enough, I need you to trust that I’m managing the rest responsibly.”
And drop the generational name-calling. Your disagreement isn’t because Dad’s a “Boomer”—it’s because he’s footing a significant bill while you’re acting entitled to the lifestyle it enables.

Dear Pay Dirt,

I moved into a new house last year, my first. Going into the holiday season, one of my big “to do’s” was to get cards and write notes and put cash in envelopes for the mailman, the person who delivers my paper each morning, and to do something, I hadn’t thought through what yet, for the many delivery drivers that leave boxes at the house. I ended up getting quite depressed and not doing any of this. At first I thought, OK, next year, but now it’s well into the new year, and I keep thinking about it, so I think I’d like to do it now and “cross it off my list.” But I don’t know what is right or appropriate.

Also logistically I can’t really figure out how it works, especially for the paper deliverer, who comes by before I wake up and throws the paper (badly, usually) from his car. I feel like I’d have to wait in my porch and run after him with an envelope, but that can’t be right? And for the delivery drivers, I was thinking of cash tips to say thank you, but how? And how much should I give these people? $20 buys nothing these days, but of course adds up. Anyway after mulling this over for way too long, I thought I would ask your advice about who, how much, and how to tip.

—Overthinking It

Dear Overthinking It,

It’s February. The holidays are over. You don’t retroactively tip your mail carrier two months later because you were depressed in December. That’s not a thing. Cross it off your list by accepting you missed it this year and letting it go.

I’m sorry you were struggling with depression during the holidays—that’s genuinely hard. But you’re using this tipping situation as a new thing to obsess over, which is just your anxiety finding a fresh home. The fact that you’re “mulling this over for way too long” (and writing to an advice columnist about it) is the symptom, not the solution.

If you actually want to show appreciation to these people going forward, here’s what’s appropriate: For your mail carrier, you can leave $20 gift card (not a cash card) in your mailbox next December with “Thank you!” written on the outside (mail carriers are not allowed to accept cash, but can accept gifts up to $20). For your newspaper delivery person (who apparently has terrible aim), tape an envelope to your door or mailbox the week before Christmas with their tip inside—they’ll see it during their route. Or, look for the “gift envelope” that many newspaper carriers enclose with the papers around the holidays. There’s no expectation to tip individual delivery drivers throughout the year. They’re different people every time.

I do think you should talk to someone about the depression that derailed you in December and the perfectionism masking your anxiety that’s keeping you stuck now. At the end of the day, this isn’t really about tipping etiquette. This is about you beating yourself up for not executing a task perfectly and then creating an impossible scenario (February tips for December holidays) that you can never live up to.

Correction, March 2, 2026: This piece originally misstated that the letter writer could give a cash gift to their mail carrier, which is against federal law. It has been updated to suggest that a $20 gift card (not a cash card) is appropriate (and legal).

—Ilyce

Classic Prudie

I am a single mom, with one daughter, dating a man with two sons. We were on the road to getting married, but that has reached a screeching halt. My boyfriend’s 14-year-old son is a Nazi.

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