Jun 5, 2025
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.
Advertisement
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.”
Advertisement
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.
Must Read
- Dave Ramsey warns nearly 50% of Americans are making 1 big Social Security mistake — here’s what it is and the simple steps to fix it ASAP
- Robert Kiyosaki begs investors not to miss this ‘explosion’ — says this 1 asset will surge 400% in a year
- Vanguard reveals what could be coming for U.S. stocks, and it’s raising alarm bells for retirees. Here’s why and how to protect yourself
Join 250,000+ readers and get Moneywise’s best stories and exclusive interviews first — clear insights curated and delivered weekly. Subscribe now.
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.
You May Also Like
- Turning 50 with $0 saved for retirement? Most people don’t realize they’re actually just entering their prime earning decade. Here are 6 ways to catch up fast
- This 20-year-old lotto winner refused $1M in cash and chose $1,000/week for life. Now she’s getting slammed for it. Which option would you pick?
- Warren Buffett used these 8 repeatable money rules to turn $9,800 into a $150B fortune. Start using them today to get rich (and stay rich)
- Here are 5 easy ways to own multiple properties like Bezos and Beyoncé. You can start with $10 (and no, you don’t have to manage a single thing)
Victoria Vesovski is a Toronto-based Staff Reporter at Moneywise, where she covers the intersection of personal finance, lifestyle and trending news. She holds an Honours Bachelor of Arts from the University of Toronto, a postgraduate certificate in Publishing from Toronto Metropolitan University and a Master’s degree in American Journalism from New York University’s Arthur L. Carter Journalism Institute. Her work has been featured in publications including Apple News, Yahoo Finance, MSN Money, Her Campus Media and The Click.
