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The Moneyist: ‘For my sister, enough is never enough’: She thinks our family’s money is hers. How do I stop her from treating me and our wealthy parents like an ATM?

Dear Quentin,

My sister and I are in our early 30s. She still has trouble understanding that other family members’ money is not her money. We come from a solidly upper-middle-class family. My parents had saved and put together an estate of about $7 million by the time my dad retired 10 years ago. 

For my sister, enough is never enough. It never mattered how much she got or how nice of a vacation we went on — there was always someone else who seemed like they were getting more from their parents than we were, and she would regularly complain about Mom and Dad being “stingy” and “not turning the tap on.”

My parents got divorced five years ago. The judge gave them a 60/40 split in the divorce, with 60% going to my dad. He became my sister’s primary target. She and her husband lived rent-free in my dad’s house, raged at him after he said no to their demands, and told him he was a bad father for not paying their credit-card debt.

“‘We lent her money that she never paid back, and probably never planned on it.’”

My sister only ever complained to me about my parents not giving her more until almost five years ago, when I met my soon-to-be husband — we get married this June — who happens to make a very nice salary at a tech company. Since then, there has been a steady increase in terms of what she seems to be expecting to get from me. 

We lent her money that she never paid back, and probably never planned on it. I try to get together with my nephew once a week, and she just started showing up and has made herself part of it when she found out I took him to lunch after preschool. She started suggesting I take them to places that cost $200 for lunch.

Most recently, she was trying to convince me to pay for her and her son to fly down to California and go to Legoland. I was hoping you might have some suggestions as to how to protect oneself in a situation like this — where the goal is to keep a relationship with my sister, but to set boundaries so she doesn’t see me as an ATM.

Thank you for any advice you can offer. 

Sincerely Frustrated Brother

Dear Frustrated,

Sometimes you need to look at what hasn’t worked in order to figure out what will work. You have dealt with your sister over a number of years in a variety of unwelcome situations. Did you believe she would ever repay that money? Of course not. You are participating in the drama by acquiescing to her requests. It’s like someone who is intent on trying a combination lock on a safe. She will keep trying to see how many times it takes to crack it.

You are both engaged in a pattern of behavior. She won’t stop. The question is, will you? As much as this annoys you, I can imagine that the outrage and/or annoyance you must feel is familiar to you now, and gins up a lot of conversations with your husband-to-be and friends of the “you won’t believe what she’s done this time” variety. It’s a thorn in your side, but we can become addicted to those thorns, as much as we hate to admit it.

“ It’s a thorn in your side, but we can become addicted to those thorns, as much as we hate to admit it.”

So what do you do? Tell her how you feel the next time she wants something for nothing: “It makes you uncomfortable when you ask for free stuff.” So here’s the warning: It likely won’t go well. You won’t get the response you need or want. She won’t see the error of her ways. She may say you’re a terrible person. If so, repeat your statement. Be prepared for, “Who, me? I only asked for X or Y. That’s what siblings are supposed to do for each other, etc.”

You don’t have to answer every call or email. Silence is a powerful tool. You can’t control her reaction or feelings. That’s not your job. Your only concern is to express your needs. Tell your parents how you choose to handle it, and they can choose to do the same, or not. That’s their choice. For every person who has difficulty laying a boundary with a pushy person, there were 50 people who did so before. It can persist for years, even a lifetime.

It’s like getting a call from a friend who constantly invites themselves to stay. You can say, “It doesn’t work this weekend.” But they will keep asking until you finally tell them to stop. Or the telemarketing company that wants you to buy a season ticket to a theater club. You can tell them, “I’m busy. I’ll think about it.” Or even, “Not today, thank you.” But until you say, “I’m not interested, thank you. Please remove me from your call list,” they won’t stop calling.

Yocan email The Moneyist with any financial and ethical questions related to coronavirus at qfottrell@marketwatch.com, and follow Quentin Fottrell on Twitter.

Check out the Moneyist private Facebook group, where we look for answers to life’s thorniest money issues. Readers write in to me with all sorts of dilemmas. Post your questions, tell me what you want to know more about, or weigh in on the latest Moneyist columns.

The Moneyist regrets he cannot reply to questions individually.

More from Quentin Fottrell:

• ‘I’ve felt like an outsider my whole life’: My father died without a will, leaving behind my stepmother and her 4 children. Do I have any rights to his estate?
• ‘He was infatuated with her’: My brother had a drinking problem and took his own life. He left $6 million to his former girlfriend who used to buy him alcohol
• She had a will, but it was null and void’: My friend and her sister are fighting over their mother’s life-insurance policy and bank account. Who should win out?

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