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.
Don’t miss
- I’m 49 years old and have nothing saved for retirement — what should I do? Don’t panic. Here are 5 of the easiest ways you can catch up (and fast)
- You’re probably already overpaying for this 1 ‘must-have’ expense — and thanks to Trump’s tariffs, your monthly bill could soar even higher. Here’s how 2 minutes can protect your wallet right now
- Gain potential quarterly income through this $1B private real estate fund — even if you’re not a millionaire. Here’s how to get started with as little as $10
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.
Read more: Want an extra $1,300,000 when you retire? Dave Ramsey says this 7-step plan ‘works every single time’ to kill debt, get rich in America — and that ‘anyone’ can do it
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.
What to read next
- Don’t have the cash to pay Uncle Sam in 2025? You may already be eligible for a ‘streamlined’ handshake with the IRS — here’s how it works and how it can potentially save you thousands
- Robert Kiyosaki warns of a ‘Greater Depression’ coming to the US — with millions of Americans going poor. But he says these 2 ‘easy-money’ assets will bring in ‘great wealth’. How to get in now
- Here are 5 ‘must have’ items that Americans (almost) always overpay for — and very quickly regret. How many are hurting you?
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
