Family loyalty can be a powerful force, but at what point does it cross into financial self-sabotage? That was the dilemma one caller brought to "The Ramsey Show," where co-hosts Jade Warshaw and John Delony tried to untangle the tricky line between generosity and enabling.
The man, who introduced himself as Roger, said he had been sending his 75-year-old married sister $700 every month for the last decade. The problem, as he explained, is that she's "never really had a job" and has relied on others her entire life. "I've been sending her about $700 a month for about 10 years," Roger told the hosts. "She's never really had a job… my wife is about to retire and the source that I'm pulling this money from is going to dry up. I'm not sure I can sustain her lifestyle."
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Delony didn't hesitate: "You can't." He quickly cut to the heart of the issue. "She's never had a job ‘cause she's never had to, right?
Roger admitted as much, explaining, "She's never worried about tomorrow." For years, he had stepped in, quietly shouldering the responsibility. "Ten years is a long time," Warshaw reminded him, pointing out that the total added up to a massive sum when he considered not just the monthly checks, but "the incidentals along the way."
The caller explained that he had lived on a modest income, but made smart decisions that allowed him to retire comfortably. Still, the royalty source he had been tapping into to support his sister was about to disappear. He wondered whether there were social services his sister could turn to at her age. Warshaw pressed him gently but firmly: "Don't you think that's hers to discover?"
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That question revealed the deeper struggle. Roger admitted his sister isn't manipulative or demanding. "She's not a guilt trip type person in this thing," he said. Yet he was still tying himself up in knots over her financial well-being. "I think it's a little bit of loyalty to her. I've seen her like three times in 30 years. It's trying to be the good guy in this whole thing."
Delony zeroed in on the guilt weighing Roger down. "Why do you take yourself on guilt trips that she's not asking you to go on?" he asked, pointing to the unnecessary pressure Roger kept piling on himself.
Warshaw picked up the thread and pressed deeper. She described it as more than just financial responsibility — a "nagging" guilt that might have roots in their shared past. "Are you trying to make up for something? Is there something you should have been there for and you weren't?"
Roger's response revealed the hold that guilt had over him. "She's family and it's like, you know, what desperation she'll go into if this money's not there. It's like pulling the plug saying, ‘Okay… I guess I'm gonna have to sleep in my car.'"
Even as he spoke, he leaned on excuses — pointing to her husband's illness and their financial struggles — to justify why he kept sending money year after year. The pattern had stretched decades, despite the fact that he'd only seen his sister three times in 30 years.
Warshaw was blunt in her response. "I do think you're enabling her. You can't enable somebody and then complain that they are failure to launch," she said. "If you're going to keep funding it, you have to do that with a glad, cheerful heart and stop talking bad about your sister."
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Delony put it even more simply: "We can't help you, my guy, because you want to do this. If you had more money to keep doing it, you'd keep doing it."
The bigger picture, they argued, isn't just about $700 checks. It's about the unspoken pressure many people feel to step in as a safety net for family, even at the expense of their own financial security. In Roger's case, it wasn't his sister who was demanding the support — it was his own sense of obligation and fear of what might happen if he stopped.
That's the tension millions of families quietly face: how long do you keep propping up relatives who never found their footing? Where's the line between compassion and enabling? And when does helping family mean hurting your own?
As Warshaw told him, generosity isn't wrong — but it has to be balanced with reality. "There is a component to this that you've also got to be able to afford," she said. "If you want to be generous, we're never going to stop you. But you said the source you were pulling from is drying up. You can't give away what you don't have."
It was a sobering reminder that supporting family can't come at the cost of sabotaging your own household. At some point, loyalty has to be weighed against boundaries, and love expressed not through endless checks, but through honest conversations.
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