A New Jersey man borrowed $20K from his brother to go to law school, but bought a car instead — then crashed it. Here's the advice he got on John Mulaney's new Netflix talk show

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.