I have the perfect scheme to pay my lifelong friend’s bills

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Dear Pay Dirt,

I am fortunate to be part of a circle of four friends who have been close since elementary school. All but one of us are happily married, have several children, and are doing well financially, but we are not rich. That one, “Penny” has expenses that consistently exceed his income, amounting to more than $10,000 a year. And every time she needs money, the other three of us have a huge fight, between us and with our husbands, over whose turn it is to help her.

Some of this is not Penny’s fault. His parents prevented him from going to university. They also both died relatively young, leaving him no money, no property and guardianship of his disabled sister. Penny also has a bunch of weird health issues that require expensive medication. Something else is: she insists on living in a “nice” apartment (which I’m a co-signer on) instead of the trailer she could afford, she refuses to look for a better job because she likes her bass – stress but low-paying retail job, refuses to try to monetize her creative hobby and overspends on objects as stress relief and DoorDash because she doesn’t like to cook. Having a partner to split the expenses with would help Penny enormously, but she’s perpetually single because she’s a very old 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 is not only a super nice guy, but also a self-made multi-millionaire who has dozens of properties and invests in small businesses as a hobby. He is about 20 years older than us, but he is quite attractive for his age. He is also single and has older wives. He asked Penny for her phone number and she gave it to him. But when she called her and they spoke one-on-one, Andy told her about his battle with metastatic melanoma and how he’s decided if/when the cancer comes back, he won’t go through the hell of chemo and radiation again ; go smoke a bunch of weed and let nature take its course. Penny told him, and then told me, that she didn’t want to be in a relationship with him because it hurt so much to lose her parents, that she doesn’t think she can go through that again.

I get it, I really do, 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 up for life, and even if she and Andy didn’t end up getting married, at least he’d be in a better position to help her than the rest of us. All three of us agree that it will 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 on how we should approach the overall Penny problem?

—Touched and marked

Dear Tapped Out,

This letter reads like a creative writing project. Still, I’ll address it head on because a lot of people need to hear this lesson: Supporting an adult financially doesn’t mean you get information about their romantic relationships. You write about the “general Penny problem” as if you were 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 an older man rich on his deathbed. But Penny is a modern, grown-up working woman who 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 great that you have such a tight-knit group that will always be there for each other. (Even if that help seems to come with disparaging comments about its size and appearance.) But there’s a difference between helping a friend out of a sticky situation and allowing a friend to make the same financial mistakes without a plan to change . If you want to help Penny get her finances under control, the answer isn’t to keep paying her bills or find her a rich husband who will do the same. It would help you find resources to live within your means, such as finding accommodation that you can afford on your income alone.

Let’s repeat the whole 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 for her phone number and she gave it to him (possibly after the host kept pestering her to do so). After speaking to the man on the phone, she discovered that he would 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.

My daughter won’t talk to me because I can’t finance her whole wedding Oh well: Netflix’s big new hit is promoting an absurd ‘theory’ about human history The biggest mystery of the white lotus isn’t who will really die The problem with the second alleged leak to the court

In that sense, Penny’s decision not to take the relationship further seems 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 just because they’re rich isn’t an insurance policy; is exploitative Penny should not be expected to trade at a loss for a opportunity to financial security. This is not a fair question to anyone.

It’s okay to talk to your friends about their dates. But using your financial aid as leverage over their dating decisions is not acceptable. Nor should you see a friend’s (or anyone’s) single status or weight as something that needs to be “fixed.” Don’t have a huge fight the next time Penny’s expenses exceed her income. Especially one where you bring up his romantic life. Instead, don’t give him money. Offer help and support to get organized, but turn off the ATM. If that financial help comes with a guilt trip for every man you let slide, it’s not worth it. Have we learned nothing? Becky Sharp?

– Lillian

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