Pay Dirt

I Have the Perfect Scheme to Get My Friend’s Bills Paid for Life

Are we being unfair?

A group of four women smiling for a photo together.
Photo illustration by Slate. Photo by Tom Kelley Archive/iStock/Getty Images Plus.

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Dear Pay Dirt,

I’m blessed to be one of a circle of four friends who have been close since elementary school. All but one of us are happily married, with several children, and doing all right financially, but not rich. That one, “Penny” has expenses that consistently exceed her income, to the tune of $10,000-plus per year. And every time she needs money, the other three of us have a huge fight, with each other and with our husbands, over whose turn it is to help her.

Some of this is not Penny’s fault. Her parents prevented her from going to college. They also both died relatively young—leaving her no money, no property, and the guardianship of her disabled sister. Penny also has a slew of odd health problems that require expensive medications. Some of it, on the other hand, is: She insists on living in a “nice” apartment (which I’m the cosigner for) instead of the trailer she could afford, she refuses to seek a better job because she likes her low-stress but low-paying retail job, refuses to try to monetize her creative hobby, and she overspends on knickknacks as stress relief and DoorDash because she doesn’t like cooking. Having a partner to split expenses with would help Penny enormously, but she is perpetually single because she’s a very big lady who doesn’t pay much attention to her appearance.

Last weekend Penny came to a party at my house and met my husband’s business partner “Andy,” who’s not only a super nice guy but a self-made multimillionaire who owns dozens of properties and invests in small businesses as a hobby. He’s about 20 years older than us but quite attractive for his age. He’s also single and into bigger women. He asked Penny for her phone number, and she gave it to him. But when he called her and they talked one-on-one, Andy told her about his battle with metastatic melanoma, and how he’s decided if/when the cancer comes back, he’s not going through the hell of chemo and radiation again—he’s just going to smoke a ton of weed and let nature take its course. Penny told him, and later told me, that she didn’t want to get into a relationship with him because it hurt so much to lose her parents, she doesn’t think she can go through that again.

I understand this, truly, but it still seems incredibly short-sighted, and typical of Penny to always put emotion ahead of practicality. She and her sister could have been set for life, and even if she and Andy didn’t end up marrying, he’d at least be in a better position to help her out than the rest of us. We all three agree it’s going to be hard not to bring this up the next time Penny asks for money. Are we being unfair to her? Do you have any suggestions for how we should address the overall problem of Penny?

—Tapped Out and Ticked Off

Dear Tapped Out,

This letter reads like a creative writing project. Still, I will address it at face value because many people need to hear this lesson: Financially supporting an adult does not mean you get input on their romantic relationships. You write about the “overall problem of Penny” as though you are the extended family of an orphaned spinster in the 1830s. If this were Georgian England, perhaps her only hope for financial security would be to marry a wealthy older man on his deathbed. But Penny is a modern, adult working woman that went from being controlled by her parents to being infantilized by her friends.

I want to address Penny’s financial situation. Of course, Penny lives beyond her means: She’s never had to take full responsibility for her finances. Why would she be motivated to change if she has friends who bail her out whenever she overspends her income, including co-signing on an apartment she can’t afford? It’s fantastic you have such a close-knit group who will always show up for one another. (Even if it seems like that help comes with disparaging comments about their size and appearance.) But there is a difference between helping a friend out of a tricky situation and continually enabling a friend to make the same money mistakes without any plan to change. If you want to help Penny get her finances under control, the answer isn’t to continue to pay her bills or find her a wealthy husband who will do the same. It would be helping her find resources to live within her means—like searching for accommodation she can afford on her income alone.

Let’s rerun the entire scenario between Penny and Andy, taking money out of the equation. Penny met a man 20 years her senior at a party once. The man asked her for her phone number, and she gave it (possibly after the host kept nagging her to do so). After talking on the phone with the man, she discovered he’d refuse treatment if his cancer returned. She decides that after the trauma of being orphaned young, she doesn’t want to open herself up to loss again.

In that light, Penny’s decision not to take the relationship further sounds like a very mature and practical dating decision. Removing Andy’s wealth from the equation makes it clear that Penny weighed her interest in him against her own needs. Dating someone only because they are rich isn’t an insurance policy; it’s exploitative. Penny shouldn’t be expected to trade experiencing loss for a chance at financial security. That isn’t a fair ask of anyone.

It’s fine to talk with your friends about their dates. But it isn’t acceptable to use your financial help as leverage over their dating decisions. Nor should you view a friend’s (or anyone’s) single status or weight as something to be “fixed.” Don’t have a huge fight next time Penny’s expenses exceed her income. Especially one where you bring up her romantic life. Instead, just don’t give her money. Offer help and support in getting organized, but turn off the ATM. If this financial help comes with a guilt trip for every man she’s swiped left on, it’s not worth the trouble. Didn’t we learn anything from Becky Sharp?

—Lillian

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