I was OK subsidizing my cheap friend. But then he dropped a bomb on me.

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.

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 his current joblessness, he reluctantly revealed the shocking truth to his money situation.

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?

—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.

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.

—Elizabeth Spiers

From: I Just Found Out My Incredibly Cheap Friend Is Heir to a Massive Fortune. (May 5th, 2021).

Dear Pay Dirt,

My boyfriend earns approximately 25 percent more than I do. (We’re gay guys, if that matters.)

We’ve always split restaurant checks and other things like that, and sometimes he buys bigger-ticket items, like a hotel during travel, and doesn’t ask for money. Now we’re planning to move in together after a few years, and he wants to split the rent and bills evenly. He feels wary about adjusting rent and bills based on our incomes for not very complicated reasons—splitting it just feels fair to him.

I know this is not hugely relevant to who should pay what, but in this arrangement, my rent will increase by 50 to 60 percent, and his will decrease by about 30 percent, because he already lives alone and I don’t, and I also am paying off more debts, so my monthly bills are higher (almost done!). This isn’t a deal-breaker for me exactly, but 1) can you give me a very declarative and personal ruling about what is fair in situations like this, and 2) how should I frame the discussion with him beyond the very basic communication we’ve done so far?

—Half and Half

Dear Half and Half,

I cannot give you a declarative ruling, because every relationship has its own unique set of circumstances. It sounds like you would be losing a lot of financial ground by moving in with him, which isn’t fair to you, nor does it make financial sense. You’re heading in the right direction with your debt (congrats!), and a significant rent increase would change that, so it’s worth having a conversation with him about it.

Start by sharing all the financial progress you’ve been making. Let him know you’d love to move forward with him, but a significant increase in living expenses would be hard for you. Explain that while it is your debt, it’s essential for your own future and your future as a couple to pay it off sooner, and a higher share of rent would mean slower progress. Then ask him if he would be willing to pay a bit more now, then reassess again in the future, once your debts are taken care of and you have more flexibility. He may say no, and if he does, that’s OK. It’s up to you to decide what’s best for you financially and for your relationship. Maybe that includes moving forward anyway. Maybe that includes delaying the move. (Relationships have no rule that states you must move in together by a certain date.) Having a healthy relationship with a wealthier significant other while maintaining a healthy relationship with your own money can be challenging, but it can be done. Keep an open line of communication and stay flexible, but know your limits.

—Athena Valentine

From: My Grandmother Says She’ll Stop Sending Me Money Unless I Get Pregnant. (May 8th, 2021).

Dear Pay Dirt,

I have some rich friends who are very open about how much money they have and what they’re spending it on—and that can get a little irksome. I understand it might be logistically complicated to renovate two houses at once on different continents, and yet … But other rich friends downplay their wealth, often a bit absurdly, and I find that even more annoying. Am I allowed to call them on their I’m-just-not-sure-if-I-can-afford-that BS? And, if so, what’s the best way to do it?

—No, You’re Not Secretly Middle Class

Dear No, You’re Not Secretly Middle Class,

Your columnist feels your pain on this one, as a person who has many friends who work in finance and run companies, and your columnist is writing for, well, perfectly-decent but not Second-Home-Acquisition money. Or, let’s face it, First Home Acquisition money.

Here’s what I think is a healthy way to look at it, and actually enjoy it, which I try to do: If these people are really your friends, you want them to be happy and not anxious and to be able to talk to you about things that they’re excited about, things they dread, things that are happening to them that you can’t personally relate to. Focus on how these things are making your friends feel and not what the things are themselves. Unless they’re complete jerks, they’re not trying to make you feel bad or self-conscious about the fact that you’re not in the same place financially.

If it really, really bothers you, a simple solution is to be more open with your friends about your own financial situation. And not so that they censor themselves, but so you can have a contextualized conversation about these things that doesn’t feel one-sided. The whole appeal of this column for me is that we live in a society where money permeates everything we do and we’re still not really allowed to talk about it, especially when what we’re talking about is not having enough money. If you think being open about this would make them uncomfortable, that’s maybe an indicator that the friendship is lacking something, not that you are.

—E.S.

From: My Husband Is Destroying Our Finances for His “Passion.” (May 12th, 2021).