Vault: Would You Loan Money to a Family Member Who Won't Work?

Summary

The Bert Show – Episode Summary
Episode Title: Vault: Would You Loan Money to a Family Member Who Won't Work?
Air Date: April 6, 2026

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Overview

In this episode, The Bert Show tackles the difficult question of whether to loan money to a family member with a history of financial irresponsibility and unwillingness to work. The hosts field a call from Cynthia, who’s torn about her cousin repeatedly requesting financial help despite a long track record of poor decisions. The discussion, filled with real listener stories and candid advice, explores boundaries, guilt, and enabling within family dynamics.

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Key Discussion Points and Insights

Cynthia’s Dilemma: The Backstory (01:05–05:27)

• Cynthia’s Call: Cynthia reaches out for an objective opinion, stating she can’t get one from her own family.
• Family History: Cynthia and her cousin grew up close, but drifted apart over the years due to different life choices and physical distance.
• Cousin’s Pattern: Cynthia details her cousin’s repeated history of bad decisions—dabbling in drugs and partying, two unplanned pregnancies by different fathers, never finishing college, not working, and relying on her enabling mother.
• Financial Help Squandered: Their grandmother gave both girls substantial money for college; Cynthia used hers wisely, while her cousin spent hers on untraceable expenses. After a car accident, the cousin received a large settlement but did not use it for intended medical expenses, leaving her still in need of surgery.

“She’s probably been given close to $100,000 from the money between my grandmother and this accident, and she has nothing to show for it. Her checking account probably has $1,000 in it, if that.” – Cynthia (04:48)

The Current Ask: Another Loan Request (05:27–06:47)

• Present Situation: Cynthia’s aunt (her cousin’s mother) is now asking Cynthia’s family for $5,000 to cover surgery and associated expenses.
• Family Pressure: Cynthia anticipates being approached for money at a family gathering, especially since she’s perceived as financially secure.

Hosts and Listeners Weigh In: Is It Enabling? (06:47–08:50)

• Panel Reactions: Across the board, the hosts and callers agree that providing more money would be enabling.
• Consequences and Responsibility: Melissa argues, “Your life is made up of the consequences of all the decisions you’ve made along the way. She’s made poor decisions along the way. Why do you have to make up for her poor decisions when you’ve been the one making good decisions?” (06:49)
• Counterpoint on Guilt: Burt raises the issue of the kids’ well-being as a source of guilt but is met with skepticism about whether any money given would actually help the children.

Stories from Listeners: Experience Speaks (08:50–10:12)

• Liz’s Story: Liz calls in, sharing her unresolved ordeal with loaning money to her husband’s family, echoing Cynthia’s fears of repayment never coming.
• The Nature of Family “Loans”: Listeners offer the adage that if the collateral is blood, the loan is a gift, not a loan. Repayment is rare, and expectations should reflect that.

“If there’s… If the collateral is blood… then it’s a gift, not a loan, is essentially what it means.” – Unidentified Commentator (09:40)

Alternatives to Cash: The “Work for It” Approach (10:04–10:38)

• Creative Solutions: Jen describes her father’s tactic: offer work instead of a pure handout. Only pay for completed work, and if the cousin doesn’t show up, she doesn’t get paid.
• Potential Pitfalls: There’s skepticism about follow-through given the cousin’s track record, but the idea is floated as a possible halfway point.

“If you want this money, then you’re gonna have to work for it… I will pay you this rate… over this portion of time, you will get the full amount that you’re asking.” – Jen (10:18)

Devil’s Advocate: Any Argument for Giving the Loan? (10:40–11:28)

• Host Challenge: Burt challenges Cynthia (and the panel) to come up with a legitimate reason to loan the money.
• Weak Excuses: Cynthia struggles to articulate a genuine rationale but mentions, “She’s, you know, trying to make a change… I want to believe that there is the girl that I used to know… I just don’t know if it’s true.” (11:06)

Emotional Tolls and Final Advice (11:28–12:32)

• Melissa’s Warning: Don’t expect peace of mind. Once you give the money, every frivolous purchase by the cousin will breed resentment.
• Panel Consensus: Everyone agrees—do not give her the cash. This is a rare, “unanimous decision” (12:30).

“A unanimous decision.” – Jen (12:30)

Preparing for Family Fallout (12:32–13:00)

• Stand Firm: Jen warns Cynthia about upcoming family pressure but advises her to "be strong to it… they’ll get over it.” (12:46)
• Dramatic Pleas Expected: Cynthia predicts her cousin will approach with a dramatic “big pitch” for the money.

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Notable Quotes & Memorable Moments

• On Enabling:
  “If you continue to give her the money… you will enable her.” – Jen (08:17)
• Family ‘Loans’ as Gifts:
  “If the collateral is blood… then it’s a gift, not a loan.” – Unidentified Commentator (09:40)
• Work for the Loan:
  “If you want this money, then you’re gonna have to work for it.” – Jen (10:18)
• Universal Agreement:
  “A unanimous decision.” – Jen (12:30)

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Important Timestamps

• 01:05–05:27: Cynthia’s backstory and cousin’s financial patterns
• 05:27–06:47: New request for $5,000—setting up the central dilemma
• 06:47–08:50: Hosts and listeners analyze the enabling dynamic
• 08:50–10:12: Listener stories and the “loans to family are gifts” concept
• 10:04–10:38: Alternative “work for money” solution
• 11:28–12:32: Final consensus and emotional considerations
• 12:32–13:00: Prepping Cynthia for family pressure and drama

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Takeaways

This episode underscores the emotional and ethical complexities of lending money within families, especially to relatives who repeatedly demonstrate irresponsible behavior. The community—a mix of hosts, guests, and listeners—unanimously discourages enabling, urging Cynthia (and listeners) to establish firm boundaries even in the face of family pressure or guilt.

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For listeners facing a similar situation, the advice is clear: past patterns predict future behavior; don't expect gratitude, and don't confuse a loan for a gift—especially when family is involved. And expect drama, but set your boundaries with confidence.

Transcript

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[Burt (Radio Show Host)]

Visit borhears.com you're on the Burt Show. Good morning, Cynthia. You are on The Birch Show. Q100. Hi.

[Cynthia (Caller)]

Hi. Good morning. Thank you. I need your help. I'm totally torn about this situation with my cousin and. Yeah, I really. I don't know what to do. I don't feel I can get an objective opinion from the family.

[Burt (Radio Show Host)]

We told earlier this morning that this has everything to do with money and borrowing money. And man, whenever you start to do stuff like that with family, it always gets a little dicey, you know?

[Cynthia (Caller)]

Absolutely. And it's like, I love my cousin and I want to help her, but there's like a long history here of irresponsibility, and I feel like that should not be rewarded. So there's a lot of details. I don't know if you want to start at the beginning and give you.

[Jen (Caller/Commentator)]

Yeah, yeah.

[Burt (Radio Show Host)]

It's all yours.

[Melissa (Caller/Commentator)]

Yeah.

[Cynthia (Caller)]

All right. So, well, my cousin and I are about, you know, just a few months apart, actually. We're both 27 and we were really close when we were younger. I was born in Tennessee and lived there for the first seven or eight years of my life. And, like, I've always kept in touch with her. We've seen each other when I would go down there for family reunions. We moved to the Atlanta area when I was in grade school. And you know, our families were very close, but, you know, there was some distance as we got older into our teenage years because we lived apart. And also she started making some bad decisions, so it was awkward. But you know, for example, I had great grades in high school and she could have had great grades, but she was kind of a partier. She got into drugs and drinking a little in high school, you know, kind of drove her parents crazy and then actually got pregnant right out of high school with a baby. Didn't marry the guy, didn't even really know the guy. It was kind of a shock to all of us.

[Melissa (Caller/Commentator)]

It was a whoops.

[Cynthia (Caller)]

Yeah. Our grandmother gave us both a substantial amount of money that would have paid for, you know, three out of four years of college, plus some living expenses. They were very generous. Gave it to us and especially to her, knowing that she was going to need some extra care. She may have even gotten a little bit more than me, but we both got a substantial amount. I used mine, I went to college, I had a part time job at college, but I didn't have to do much because I had that lovely extra fund. And I've done very well for myself. I mean, I started my own business a couple years back. I'm doing pretty well financially. I'm pretty stable. And she's completely the opposite. She never went to school. She used that money for who knows what, partying and like, she's never even really taken responsibility for herself, much less her child. She lives at home with her parents still, you know, we're 27. She's still living at home. She got pregnant a second time three years ago by a totally different guy and now has two kids and her parents take care of them. She lives at home. She doesn't work. Like, she doesn't work at all. Yeah, she doesn't work. She's like, she's. Well, she, you know, she needs to be home to take care of the kids, but she's not taking care of the kids.

[Liz (Caller)]

So her parents. So her parents support her?

[Cynthia (Caller)]

Yeah, yeah. Her mother totally enables her. Like, I can't even. Like that is another whole issue. But. But you know, and then she had a car accident about. I guess it's five or maybe five or six years ago. It was before the second baby, so that's all I really remember. And it wasn't her fault. She did get hit going through a green light and somebody Else ran a red light and plowed right into her and crushed her left arm on the driver's side. She ended up getting a settlement from that. And I don't know, it was. We're not really sure how much it was, but it was tens of thousands of dollars. I'm guessing maybe 40,000, maybe even 50. I don't know, maybe even more.

[Burt (Radio Show Host)]

So here, what you're establishing is time and time again, money has been thrown her way, and she's not doing anything responsible with it. She just seems to be.

[Cynthia (Caller)]

That money was that in case, you know, she needed any medical expenses, she might have needed some surgery or something. She did not spend that money on any physical therapy or rehab or anything. A part of it was for that. And so, you know, now down the road, a few years later, her arm, the mobility of her hand is really messed up. Now she does need surgery, and all that money's gone. So not working. She got two kids. She lives at home with a parent. She's blown. She's probably been given close to $100,000 from the money between my grandmother and this accident, and she has nothing to show for it. Her checking account probably has $1,000 in it, if that.

[Burt (Radio Show Host)]

Okay, so now we have history here. So I'm assuming you know that she's coming to you for the next loan.

[Cynthia (Caller)]

Well, that's it. That's the thing. Now she needs surgery on her hand. They went. Her mom actually called my mom and was like, I'm so sorry to ask, but if you could just give us a little bit for the. For the surgery part and maybe a little towards. They asked my mom for $5,000.

[Burt (Radio Show Host)]

Everybody in here shaking their head now.

[Unidentified Caller/Commentator]

Yeah, Jen's been waiting to.

[Cynthia (Caller)]

She wants to help, but she's, you know, needing to worry about her future, her retirement, and with the economy and the stock market the way it is, she's totally screwed. So she called me and said, I want you to be. I'm going home for Memorial Day weekend. And so everybody's going to be there, and my cousin's going to be there. And my mom said, I just had this feeling that they're going to be coming to you for money because everybody knows you're doing really well, you know, and they feel like I don't have any responsibility because I don't have children yet. But, hello, I have myself in my life, and I've worked really hard. Like, I'm just torn because I could give her this money. Like, it wouldn't kill me to do it, you know? I'm not looking forward to taking out

[Jen (Caller/Commentator)]

the same conversation has gone on her head over and over that swirl. Well, I could, but I don't want to. Da da da da da.

[Burt (Radio Show Host)]

Yeah. 404741. Q100. So your question is, do you go ahead and do you give the cash or do you hold onto it? Do you continue? It feels like enabling to you.

[Cynthia (Caller)]

It does if you give. I love her.

[Melissa (Caller/Commentator)]

So it's like, yeah, I say no because you know what? Your life is made up of the consequences of all the decisions you've made along the way. Right. So you've made good decisions along the way. She's made poor decisions along the way. Why do you have to make up for her poor decisions when you've been the one making good decisions? My best friend is going through something very similar with her husband's family right now. And they, my best friend and her husband have worked so hard to create the life that they have established. They didn't come from anything, but they have created a beautiful life together. They have a child, but then there is extended family on his side that are coming to mooch off of it and coming to, you know, coming to ask for, ask for handouts when they've been the ones making bad decisions all along. No, it's not your responsibility. And I mean, although it is her health and that sort of thing, if it starts with this, it's gonna end with something else.

[Burt (Radio Show Host)]

Let me just play devil's advocate. So would you have any guilty feelings if you didn't give the cash because of the kids?

[Cynthia (Caller)]

Well, that's the thing. It's like they didn't ask to be brought into a situation with an irresponsible mother. And you know, she's saying now, oh, well, I might not be. She was going to go be a bartender. She doesn't really have any other skills. And she's like, my hand doesn't work. So it's like, yeah, the kids, if they have a deadbeat mom, but how do I know she's not gonna go out and just party with that and like, you know, get injections in her lips or something? I don't know. Her priorities are kind of screwed up.

[Burt (Radio Show Host)]

So Melissa is just sitting there looking ready to tee off.

[Jen (Caller/Commentator)]

Yeah, well, I say no. I mean, because. Just because regardless, if you get, you know, crap from your family, anything, the enabling you will enable her. I mean, like Jen said, you'll enable her if you continue, if anybody continues to give her the money. Because there are plenty of people out there that have medical conditions that have no money and no resources to go to and find a way to get it done because they're responsible for their own life. And so this woman's not responsible, and she thinks she can get handouts, and that's what she's lived off of. That's what she's used to. And yeah, I say, no, you have to be hard line. No, you have. You've had money. You don't have money anymore. It's your situation. Figure it out for yourself.

[Burt (Radio Show Host)]

Liz wants to give you some advice on this. Hey, Liz.

[Liz (Caller)]

Good morning.

[Burt (Radio Show Host)]

You're on the Burt show on Q100. Hi.

[Liz (Caller)]

Hi. This is Liz.

[Cynthia (Caller)]

Hey.

[Melissa (Caller/Commentator)]

Hey.

[Jen (Caller/Commentator)]

Hey.

[Liz (Caller)]

I just went through this with my husband and his mom, and they. Three people live in their household, none of them work. And they came to us and asked us for $700. And my. It was. I had to choose between my husband or the money. And, you know, everything weighed down. And, you know, it was my marriage on the line, so I had to, you know, I gave up the money. And, you know, she was like, well, I'll pay you back. I'll pay you back. And it's been a year, we haven't seen the money.

[Burt (Radio Show Host)]

Yeah. Somebody told me a long time ago, once you. Once somebody borrows money from you, you have to sort of go on thinking that you're never getting that money back.

[Unidentified Caller/Commentator]

Somebody. I wish I could remember the phrase, but like, my. My dad says it about some people in the family that, like, if there's. If the collateral is blood, you know what I mean, Then it's a gift, not a loan is essentially what it means. So if you're giving the money to someone because of your cousin, brother, sister, aunt, uncle, nephew, niece, grandmother, then it's not alone. It's not alone.

[Jen (Caller/Commentator)]

That happens with some friends, too. But I think also a tactic that my dad would do if somebody asked him for money is work it off so you could all of a sudden become her boss.

[Cynthia (Caller)]

And.

[Jen (Caller/Commentator)]

And you don't pay her all in one thing. You pay her a little bit. And she does work to get. Because nobody has taught her to work for her money.

[Burt (Radio Show Host)]

Right.

[Jen (Caller/Commentator)]

So that's the thing is you say, look, if you want this money, then you're gonna have to work for it. So here's the schedule. This is what I need you to do, and I will pay you this rate in this amount of time and over this portion of time, you will get the full amount that you're asking.

[Unidentified Caller/Commentator]

Yeah, but what happens when she doesn't

[Jen (Caller/Commentator)]

show up, then she doesn't get the money and it's done.

[Unidentified Caller/Commentator]

Oh, so you're paying her by. She's your employer, so you don't give her $1,000 now. You give her $100 a week for the next 10 weeks.

[Jen (Caller/Commentator)]

She's your employee. And if she doesn't show up for work, she's fired.

[Burt (Radio Show Host)]

Hey, Cynthia, I'm frantically looking for somebody that says that you should give her cash, and I can't find anybody. So if you were going to argue the point that you should give her the money, what would that argument sound like?

[Cynthia (Caller)]

Well, she's, you know, trying to make a change. I don't know if I believe that, but let's play devil's advocate.

[Jen (Caller/Commentator)]

She can't even say it.

[Burt (Radio Show Host)]

So unreachable. I can't even think of one good reason.

[Cynthia (Caller)]

Changes for the children. She wants to do better. I mean, it's laughable because of her history, but, I mean, if I want to believe that there is the girl that I used to know that had some sort of ethic, work ethic, you know, life goal, I want to believe that. I just don't know if it's true.

[Melissa (Caller/Commentator)]

I think if you give her the money, every single thing that she does that is not a necessity is going to drive you up a wall. Like if she has any sort of orders a pizza for dinner, she orders a pizza. If she has on a new top, if she is wearing new jewel. I mean, I don't care if it was two bucks at Claire's that she got these new earrings from. You're gonna be infuriated by it. So just be prepared for that. Because, yeah, you see people who have, like, you know, hot pink cell phone sleeves, but they can't pay their electric bill.

[Cynthia (Caller)]

You know what I mean?

[Melissa (Caller/Commentator)]

It drives you crazy. Like, oh, they had to have that, you know, sexy addition to their.

[Jen (Caller/Commentator)]

Or just the phone itself. Or just the phone itself.

[Melissa (Caller/Commentator)]

Well, yeah, but. You know what I'm saying. I mean, it's just those frivolous exceptions, accessories or things that just are completely unnecessary that she could be spending that money on that you've given her, and it's going to send you through the roof. Yeah.

[Burt (Radio Show Host)]

Cynthia, let's check back with you early next week. I just can't find any calls. There's not a real sense of debate here because across the board, everybody is telling you what you already know, and that's to not give her the cash.

[Jen (Caller/Commentator)]

A unanimous decision.

[Burt (Radio Show Host)]

How about that?

[Cynthia (Caller)]

It happened.

[Burt (Radio Show Host)]

Mark it down.

[Cynthia (Caller)]

We can totally check in. That'd be awesome. I'll let you know how it goes. All right.

[Radio Host (Ad Read)]

Get some.

[Unidentified Caller/Commentator]

You know what that means, right? She's going to do exactly the opposite.

[Jen (Caller/Commentator)]

Just be prepared for family pressure and be strong to it. Don't have all these, you know, lobbyists in your family telling you to give her the money when you don't want to. They'll get over it. They'll get over it.

[Burt (Radio Show Host)]

I want to hear what the big pitch is, though, like how she approached you.

[Cynthia (Caller)]

It's going to be dramatic.

[Burt (Radio Show Host)]

I know it is. Thanks for sharing your story with us. Appreciate it. You're on the Birch show.