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.
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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.
Being a good friend
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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Stuck in a tough spot
Dylan found himself in a messy situation. Not only did he lie to his brother about using the $20,000 loan for law school, but now he has no way to pay it back. He mentioned buying a van for $500, which led Roy to suggest he start a side hustle — like driving for Uber — to begin earning money.
According to LendingTree, 38% of Americans have a side hustle, whether it’s delivering food, freelancing or picking up seasonal work. For many, these gigs aren’t just for extra cash: 61% say their life would be unaffordable without one.
But earning money is only part of the solution — Dylan also needs to come clean. His brother still believes he’s in law school.
“I would talk to your brother and come up with a good faith repayment plan of however much you can commit to,” Roy advised.
Dylan should also consider building a budget to get his finances back on track. That means taking stock of any income — including side hustle earnings — and mapping out monthly expenses like gas, food and debt payments.
Even setting aside small amounts consistently — say, $50 or $100 a week — can build momentum toward repaying the loan. Beyond that, budgeting can help Dylan understand where his money is going, avoid future financial missteps and rebuild trust — not just with his brother, but with himself.
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This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
