When a loved one is in need, lending a helping hand can feel like second nature — even with a price tag.
On a recent episode of his new Netflix talk show, Everybody’s Live With John Mulaney, the comedian explores what it really means to help someone — and the consequences that can follow.
He’s joined by actor Michael Keaton and Jessica Roy, a personal finance columnist for the San Francisco Chronicle. Their first caller was Dylan from Montville, New Jersey, who borrowed $20,000 from his brother to attend law school. But instead of cracking open textbooks, Dylan bought a car. Then he crashed it. After selling the wreck for scrap, only $1,200 of the original $20,000 remained.
Now, Dylan finds himself in a bind: no money, no law degree, a totaled car and a $20,000 lie he has to repay.
It’s a cautionary tale and one that might hit closer to home than you’d expect. Whether you’ve loaned money to a loved one or considered asking for help yourself, navigating finances within personal relationships can be tricky.
When money enters the mix between friends and family, the emotional toll can often outweigh the financial loss. A LendingTree survey found that 31% of Americans are owed money by a loved one — with friends and siblings being the most common borrowers.
The top reason? Covering debt payments and everyday expenses like meals and gas. But personal lending often comes with strings attached: nearly half of the respondents said they regretted lending money to someone close, and one in six admitted it had damaged a relationship.
In the episode, Roy emphasized that lending money to someone you care about requires a mental shift.
“Any money you loan someone you need to be psychologically detached from it,” she explained. “It’s a gift and I’m not going to get it back.”
It’s a mindset that protects more than just your wallet — it safeguards your relationships, too. When lending to friends and family, boundaries are just as valuable as budgets.
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