For Jenna from New York, what should have been a simple yes-or-no decision has resulted in sleepless nights. Her friend — someone she hadn’t spoken to in three years — suddenly reached out, asking for $900 to cover a lien on a storage unit she said held all her worldly possessions. The money, the friend said, was due in just a few days.
Jenna could scrape the money together, but it would be a stretch. She’s been working to pay off her mortgage and knew that handing over nearly $1,000 would set her back. Guilt gnawed at her: What if the situation were reversed? What if she really was her friend’s last hope?
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But when Jenna called The Ramsey Show for advice, hosts Ken Coleman and Jade Warshaw didn’t hesitate. Their verdict? A “hard no,” and a warning that, in their view, acting on guilt can result in self-sabotage.
Making decisions based on boundaries
Borrowing from or lending to friends and family may make some squeamish, but it’s incredibly common. A JG Wentworth survey published in August found just under 52% of respondents had borrowed money from a friend or family member at least once, and 53% had lent money. Nearly half of those who borrow from family members expected no repayment, highlighting informal financial support as a crucial resource (2).
But a loan to someone who fell out of touch and suddenly pops in to ask for money? That’s where Coleman and Warshaw started to challenge Jenna’s gut instinct. When asked how she felt the moment her friend requested the $900, Jenna admitted her first reaction was pity.
“And you just told us that $900 is a hardship that would be brought on yourself to help somebody pay off a debt. And this somebody’s not even in your life,” Coleman responded. “They haven’t even returned your calls. They haven’t even had the common decency to return a text. This is a hard no from me.”
As the conversation unfolded, the details got worse. Jenna had called the storage company herself and learned that her friend’s debt was actually double what she claimed and that she was behind on multiple units.
“That tells me … she’s hitting several people up for $900,” Coleman said.
Warshaw added: “Guilt and generosity don’t live in the same house. You don’t give out of guilt; you give out of the abundance of joy.”
If Jenna truly felt moved to help, they advised, she had to treat it as a gift, not a loan — and be prepared never to see that money again.
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The fine line between helping and enabling
Jenna’s story strikes a nerve because it’s familiar to many people. Financial experts say there’s a difference between helping someone going through a rough patch and enabling bad behavior.
According to nonprofit credit counselor InCharge Debt Solutions, enabling happens when providing one-off financial support escalates into a habit. To prevent that, the organization suggests that when providing help in an emergency, you have a discussion about how to manage similar situations in the future, including by building an emergency fund for unexpected expenses.
They also say it’s OK to ask for the borrower’s budget and a detailed plan of how the money you give will be spent. If it’s at all possible, give a gift, not a loan — nothing fractures relationships like a debt hanging over your head. Similarly, they suggest offering non-financial help if money isn’t in the cards for you. They suggest chipping in with childcare, transportation or meals at your home, and to be wary if the person says cash is the only solution (3). Perhaps Jenna could reconnect with her friend and offer support in other ways.
Finally, don’t let helping others get in the way of your needs and goals. A March 2025 report from Savings.com said parents who continue to support their adult children are often putting more money toward their kids than toward their own futures — spending more than twice as much helping grown children as they contribute to retirement each month (4).
How to say no without losing your peace
If you find yourself in Jenna’s position, the first step is to separate emotion from math. Before you agree to anything, ask yourself: Can I give this money away with no expectation of getting it back, and without damaging my own goals? If yes, go ahead. If not, then that’s OK. Next, communicate clearly. Skip elaborate justification. A simple “I’m sorry, I can’t afford to help financially right now” is enough.
If you genuinely want to help but can’t afford to pay, look for non-financial ways to do it. Offer to help your friend budget, connect them with local resources, or provide emotional support. But avoid playing the role of chronic rescuer, as it can trap both.
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Article Sources
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Ramsey Show Highlights (1); JG Wentworth (2); InCharge (3); Savings.com (4)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.