It's not uncommon for a younger sibling to need help from an older one—or for adult kids to lean on their parents now and then. But when a 46-year-old woman keeps asking her 27-year-old little brother for money, despite already owing their mom $800, it stops being family support and starts sounding like financial absurdity.
That's exactly what Dave Ramsey and John Delony thought when a caller named Brandon phoned "The Ramsey Show" from Denver. His problem wasn't a budget—it was boundaries. His much older sister had just texted him asking for $100.
"I wanted to offer her advice," Brandon said, "but I feel like she's going to be like, ‘Okay, what is this 27-year-old punk trying to school me on anything?'"
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Ramsey didn't hold back.
"He's the one with the hundred dollars you don't have. That's what he is," he shot back—then followed it with the sharpest blow of the call:
"She's an entitled brat. That's what she is."
Delony picked up from there, making it clear Brandon wasn't the one creating the problem.
"You didn't cause the rift. The rift was thrown at you," he said. The solution? A clear, calm boundary. "No, I'm not going to loan you a hundred dollars. Thank you, though."
Anything after that, Delony warned, is just trying to soften a line that needs to stay firm.
Still, Brandon admitted he felt conflicted. He hadn't answered her text because he didn't know what to say. This wasn't the first time she'd asked, either. In fact, it was the fifth. She'd also once asked him to co-sign a car loan for her daughter. He'd refused that too.
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Delony told him this visit home could be an opportunity to finally say what's needed—face to face.
"Take her out to lunch," he said. "Say, ‘I care about you. I know you've struggled. But I don't think this is about $100. Something's not right.'"
Then came the moment that cut to the heart of it.
"You just asked your little brother for $100. You're not OK," Delony said. "That gives you permission into speaking to hers and what's going on in her soul."
Ramsey echoed the sentiment.
"I know it feels weird because you're old enough to be my mother," he told Brandon. "But this is where we are."
The hosts were aligned: this wasn't about a one-time loan. It was a chronic pattern, and no amount of money was going to fix it. Enabling would only drag Brandon down with her.
"It's like giving a drunk a drink," Ramsey said.
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Brandon admitted that his parents still cave in and give his sister money, which only frustrates him further. But Ramsey shut that down too—reminding him that while he can't control his parents, he can control how he responds.
"I'm willing to help my sister in a way that actually helps her," Ramsey said. "Not in a way that keeps her stuck."
The key, they agreed, is to make this the last conversation about money.
"The next time she calls for cash," Delony said, "you just say no. No lecture. No explanation. She'll already know what it means."
And Ramsey delivered the bottom line:
"Under no circumstances do you give her a hundred dollars—unless she's doing something that'll help her never have to ask again."
For Brandon, it wasn't really about $100. It was about refusing to be a crutch for someone twice his age who should know better. And for anyone stuck in a similar dynamic—older sibling, parent, or friend who keeps turning their financial mess into your problem—the message was clear: you can love them, care about them, and still say no.
Especially when they're old enough to be your mother.
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