I plotted a way to make my lifelong friend pay the bills

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Dear Pay Dirt,

I have been lucky enough to be part of a circle of four close friends since elementary school. All but one of us are married, have several children and are doing well financially, but not wealthy. This one, “Penny,” has expenses that consistently exceed her income, by more than $10,000 a year. And every time she needs money, the three of us argue, among ourselves and with our husbands, about who should help her.

Some of this isn’t Penny’s fault. Her parents prevented her from going to university. They also both died relatively young, leaving him no money or possessions, and guardianship of his disabled sister. Penny also has a host of weird health issues that require expensive medication. Part of it, though, is this: she insists on living in a “nice” apartment (which I co-sign) instead of the trailer she could afford, she refuses to look for a better job because she loves her low-stress but low-paying retail job, refuses to try to monetize her creative hobby, and she spends too much on trinkets to relieve stress and DoorDash because she doesn’t like to cook. Having a partner to split the expenses with would help Penny immensely, but she’s perpetually single because she’s a very tall lady who doesn’t pay much attention to her looks.

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 a self-made multi-millionaire who owns dozens of properties and invests in small businesses as a hobby. He is about 20 years older than us but he is quite handsome for his age. He is also single and likes 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 decided if/when the cancer came back, he wouldn’t cross the line anymore. chemo and radiation hell—he’s just gonna smoke a ton of weed and let nature take its course. Penny told him, and told me later, that she didn’t want to have a relationship with him because it hurt so much to lose her parents, she doesn’t think she can go through that again.

I get that, really, but it still seems incredibly myopic and typical of Penny to always put emotion before practicality. She and her sister could have been fixed for life, and even if she and Andy didn’t end up getting married, he would at least be in a better position to help her than the rest of us. We all three agree that it will be hard not to talk about it the next time Penny asks for money. Are we unfair to her? Do you have any suggestions on how we should fix Penny’s overall problem?

— Typed and ticked

Dear Typed,

This letter reads like a creative writing project. Still, I’ll take it literally, because many 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 a spinster orphan in the 1830s. If this were Georgian England, her only hope for financial security might be d to marry a rich old man on his deathbed. But Penny is a modern, grown, working woman who has gone from controlling her parents to infantilizing her friends.

I want to talk about 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 exceeds her income, including co-signing an apartment she can’t afford? It’s fantastic that you have such a tight-knit group that will always show up for each other. (Even though it seems like this help comes with derogatory comments about their size and appearance.) But there’s a difference between helping a friend out of a sticky situation and continually allowing a friend to do the same things. money mistakes without any change plan. 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. This would help her find resources to live within her means, such as finding a home she can afford on her income alone.

Let’s go through the whole scenario between Penny and Andy, removing the money from the equation. Penny met a man 20 years her senior at a party. The man asked her for her phone number and she gave it (possibly after the host pestered her to do so). After talking on the phone with the man, she found out he would refuse treatment if his cancer returned. She decides that after the trauma of being an orphan at a young age, she no longer wants to open up to loss.

In that light, Penny’s decision not to go any further in the relationship feels like a very mature and practical dating decision. Taking Andy’s wealth out of the equation, it’s clear that Penny weighed her interest in him against her own needs. Dating someone just because they’re rich isn’t an insurance policy; it is exploitation. Penny shouldn’t be expected to trade a loss for a chance to financial security. This is not a fair request from anyone.

It’s good to talk with your friends about their dates. But it’s not acceptable to use your financial aid as leverage over their dating decisions. You also shouldn’t view a friend’s (or anyone else’s) single status or weight as something to “fix.” Don’t argue the next time Penny’s expenses exceed her income. Especially the one where you talk about his love life. Instead, don’t give him any 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 she’s let down, it’s not worth it. Didn’t we learn anything from Becky Sharp?

—Lillian

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