I'm 63 And Getting Re-Married, Should We Combine Finances?

Summary

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The Ramsey Show Highlights

Episode: I'm 63 And Getting Re-Married, Should We Combine Finances?
Date: August 16, 2025
Hosts: John Delony & Jade Warshaw
Caller: Aaron

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Episode Overview

This episode features Aaron, a 63-year-old widow who recently got engaged to her high school crush. With her financial future and a significant discrepancy in assets (including her fiancé’s $180,000 medical debt), Aaron calls in to ask whether she and her soon-to-be second husband should combine their finances after marriage. The hosts, John Delony and Jade Warshaw, provide practical advice and delve into the emotional and financial dynamics of late-life remarriage, blending assets, and protecting oneself.

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Key Discussion Points & Insights

1. Starting Over with a High School Sweetheart

• Aaron's Situation:
  • Widowed at 63, newly engaged to her first crush.
  • Reconnected via Facebook:
    • “Yes, it was request John Deloney won. Yeah.” - Aaron [00:48]
  • Long-distance relationship (East Coast vs. Midwest).
  • Plans to sell her house in D.C., move for affordability and family proximity.

2. Finances & Debt: Transparency is Crucial

• Asset Differences:
  • Aaron has significant equity, investments, and will likely inherit several million dollars.
  • Her fiancé has $180,000 in medical debt (from a botched surgery) and less overall wealth.
  • Both are generally debt-free, except for mortgages and the medical bill.
• Hosts’ Advice:
  • Full Disclosure:
    • “Before you sell your house and buy a new one next to him, I would love for you all to pull. Pull credit reports together and walk through it.” - Jade Warshaw [04:12]
    • Review and share full credit histories and all assets/liabilities before making major moves.
  • Combining Finances:
    • “If you marry him, that 180 grand is yalls debt.” - Jade Warshaw [04:45]
    • Marriage means financial togetherness, but not at the expense of blind trust.

3. Emotional Concerns & Due Diligence

• Addressing “the Other Shoe”:
  • The hosts urge caution about unknowns even with "high school flames who reconnect."
  • “There’s got to be some due diligence.” - Jade Warshaw [03:44]
• Initiative in a Partner:
  • Jade encourages Aaron to communicate boundaries and the type of partner she seeks:
    • “For me to feel safe is that I’m married to a guy with some initiative that... he’s on the phone making it right.” - Jade Warshaw [05:14]
• Not Just About Money:
  • “This is not a money thing.” - John Delony [03:16]
  • Emotional safety and mutual honesty matter as much as dollars.

4. Skepticism About Clearing the Medical Debt

• Challenging Optimism:
  • Hosts question the likelihood of the hospital simply erasing $180,000 even in a clear-cut malpractice scenario.
    • “If it was truly that cut and dry.” - John Delony [07:15]
  • Don't bank your future on a best-case legal or financial scenario.

5. Large Wealth Disparity & Protecting Yourself

• Asset Protection:
  • Aaron will have a large financial advantage and imminent inheritance.
  • Jade gently but firmly suggests considering legal protections:
    • “This is one of the rare moments when I'm going to strongly recommend you walk in with a [prenup]...because there's such a gap there that you all sit down and discuss.” - Jade Warshaw [08:33]
• Open Conversations:
  • Discuss future inheritances and what each partner expects regarding the sharing (or separation) of major windfalls.

6. Premarital Counseling is Essential

• Core Recommendation:
  • “Would you at least recommend premarital counseling? ...before we think prenup.” - John Delony [09:15]
  • “I think you do premarital counseling before you do everything. Yes.” - Jade Warshaw [09:25]
  • Both hosts stress that professional guidance is fundamental before mixing finances or signing legal documents.

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Notable Quotes & Memorable Moments

• On full financial transparency:
  “It's not unloving, it's not unromantic, it's not un-Christian...for you to say, hey, we're both going to bring our credit reports to the table.”
  — Jade Warshaw [07:16]

• On relationship boundaries:
  “You can't work on him. You can say...here's what I'm looking for in a partner. And it's a big deal to me that for me to feel safe...that he's on the phone making it right.”
  — Jade Warshaw [05:14]

• On being realistic about future promises:
  “It sounds like a story, too. Oh, yeah, we'll just get it taken care of...if it was truly that cut and dry.”
  — John Delony & Jade Warshaw [06:38 & 07:12]

• On large asset discrepancies in marriage:
  “Then he's gonna have a cousin somewhere that thinks he just won the lottery...So that would be my recommendation because there's such a gap there...”
  — Jade Warshaw [08:33]

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Timestamps for Important Segments

• 00:21 — Aaron introduces her question about finances and remarriage
• 02:08 — Aaron discusses her fiancé’s $180,000 medical debt
• 03:44 — Jade advises on due diligence and reviewing credit reports
• 04:45 — Jade explains the reality of inheriting a partner’s debt in marriage
• 05:14 — Conversation about communicating expectations and initiative
• 07:16 — Honest conversation about wealth, inheritances, and transparent credit checks
• 08:33 — Jade recommends a prenup due to wealth gap
• 09:15 — Recommendation for premarital counseling before considering legalities

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Episode Takeaways

• Combine finances in marriage, but only after full disclosure of debts, assets, and future expectations.
• Large differences in wealth warrant legal and financial safeguards like a prenup.
• Premarital counseling is a non-negotiable step for healthy conversations and planning.
• Be honest about what you need in a partner and relationship, especially in later-life marriages involving significant assets.
• Don’t make major financial moves based on optimistic assumptions—do your due diligence.

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This episode blends personal storytelling, practical money advice, and heartfelt relationship wisdom—true to the Ramsey tradition of equipping listeners for both financial and life success.

Transcript

[Aaron]

Brought to you by chm, a biblically based alternative to health insurance. Learn [e-mail] budget I am a 63 year old widow and I just got engaged and I am wondering, after marriage, should I combine my finances with my soon to be husband?

[John]

Yes.

[Dawn]

Yes. And congratulations.

[John]

Yeah, how about that?

[Aaron]

And the thing is, he was my high school crush, bro.

[John]

Come on.

[Dawn]

I love, I'm a huge Dawson's Creek fan, so I love this. This is awesome.

[John]

Great reference. I think America wants to hear a short version of how this happened. Obviously, a horrific loss for you. How did you reconnect with the high school crush?

[Dawn]

Guaranteed Facebook.

[Aaron]

Yes, it was request John Deloney won. Yeah.

[John]

Nice. Okay, and how, how long have you guys been dating before getting engaged?

[Aaron]

We started in November and we got engaged a little over a month ago.

[John]

Okay.

[Dawn]

Are you living in the same community?

[Aaron]

No, no, no. He, I am on the east coast, he's in the Midwest.

[John]

What's going to happen?

[Dawn]

Have you all seen. Yeah.

[Aaron]

Well, it's very expensive to retire in Washington D.C. so I will sell my home. I'll buy a less expensive home in the Midwest where he lives and where my family's from, and then I'll be completely debt free. The only debt I have now is my mortgage because my late husband was a Dave Ramsey fan and set me up for success even after he left.

[John]

So when are you guys getting married?

[Aaron]

Next year.

[John]

Okay. The way you said that, I could have heard it wrong, but the way you said it, it sounded like, I'm going to buy a home. There was no we.

[Aaron]

Yes, I have quite a bit more money than he does and he has $180,000 in medical debt.

[John]

Okay.

[Aaron]

Now, the thing is, it was a botched surgery. We had proof the surgery was botched. I'm trying really hard to get him to sue the hospital for malpractice because my thought is, in all likelihood they will just drop the debt and we can each go on our merry way.

[John]

Well, let me ask you this. Did you combine finances with your first husband?

[Aaron]

Yes. We shared everything.

[John]

So I'm going to guess here, the only thing that's giving you pause, which would create this urgency to call us today and say, hey, should I. Is this $180,000 in medical debt?

[Aaron]

Yes, because otherwise he's very responsible financially. Except for the medical debt and his mortgage, he lives debt free. He does not use credit cards. He pays cash for everything.

[John]

Are you guys planning to live in this house that you buy?

[Aaron]

Yes.

[John]

Okay, John, I, I, this is, I feel like, this is in your lane here. This is not a money thing.

[Dawn]

Okay, Aaron, how much it is kind of. Aaron, how honest can I be with you? Can I be direct since we're best friends now?

[Aaron]

Oh, yes.

[John]

He says that to everybody.

[Dawn]

I do. I do. I don't have any best friends, so I try to pick them up from show callers. Here's the deal I want. I guess I wouldn't have a job if old flames who re reconnected on social media told each other 100% of the truth. And so what I hear a lot of is, oh, yeah, no, I know he is fill in the blank. Or I know she is fill in the blank. And then people move across the country, they sell out, they cash out, they send money, they help with X, y, and z. And then there's this other shoe that drops. So I guess what I want to say for you and for everybody listening, and you may have already done this, is there's got to be some due diligence. What does that mean? Before you sell your house and buy a new one next to him, I would love for you all to pull. Pull credit reports together and walk through it.

[John]

Have you guys done that?

[Aaron]

Probably not yet, but I do plan on sitting down and doing that. And as far as selling my house and moving there, this is my hometown. My parents are still alive. All my family is there. I have nobody here.

[Dawn]

Okay, so you're going there anyway.

[Aaron]

Let's just say do that anyway.

[Dawn]

Perfect. Perfect. Okay. The second thing is, is you making peace with the following. If you marry him, that 180 grand is yalls debt. And often the money becomes the proxy war for, I want to marry this guy, but I also want to marry a man with a little bit of initiative. And he won't even. He won't even call a lawyer for 5,000 bucks and have him write a letter to clear 180 grand.

[Aaron]

Right. And. And I am going to work on him on that when I see him next month.

[Dawn]

You can't work on him. You can say, I would. I would challenge you to use this language in this next marriage. That's going to be my last one I'm ever a part of. Here's what I'm looking for in a partner. And it's a big deal to me that for me to feel safe is that I'm married to a guy with some initiative that when some. When grave injustice is done to somebody, including him, that he's on the phone making it right. And then he gets to. If you come in and say, you need to and you need to, and you need to, man, he's going to clam up like. Like all of us would. Right. Because he's going to feel the shame and the frustration and the, hey, can we just move past this? And. And hey, by the way, you've got a whole bunch of money. You can just pay it off when we get. And it's you saying, here's what I want in this new marriage.

[John]

Isn't it okay for her to ask for closure on this issue because it gives her massive heartburn.

[Dawn]

Yes.

[John]

To realize that she might be inheriting 180,000. It doesn't make it about love or relationship, but just her fear of this issue. And that's what I was getting at, that it seems like they're on board with money. Theoretically, you guys are on board. But yeah, the idea of living separate, finances and all that, just because he's got this, by the way you described it as, it's not his fault.

[Dawn]

Yeah.

[John]

I mean, any one of us could go in for a surgery and it get botched and we're stuck. You know, it's like, no one did anything irresponsible here.

[Dawn]

But that also sounds it. Also, I'm telling you, Aaron, I hope I'm wrong. It sounds like a story, too. Like, oh, yeah, we'll just get it taken care of. They screwed this up and we'll get it squared. Because if it was that easy, if they botched it, I've heard of head of hospitals coming in and saying, hey, we're going to clear this debt and we're also going to pay you $50,000 as some sort of entry settlement to just end this thing.

[John]

I had the same feeling, John.

[Dawn]

So there's, there's something.

[John]

Aaron. I don't want her to bank on that. It feels like, Aaron, the way you set that up, you're banking on, well, you know, we get a lawyer involved, they're probably going to wipe it away. And when you said it, I went.

[Dawn]

They probably would have if it was truly that cut and dry.

[John]

Yeah.

[Dawn]

All that I want you to hear me say is I want you to do your due diligence. And it's not unloving, it's not unromantic, it's not un. Christian. Whatever you want, whatever adjective you want to put there. It's none of those things for you to say, hey, we're both going to bring our credit reports to the table. I want to see where we both are. And if he says, oh, we don't need to do that. I told you, I'm debt free. Say, yeah, I know, I want to see this, what I'm walking into. And then he gets to decide, do I want to be married to an amazing woman or am I going to let my ego run wild and I may not have been telling the full truth. Here's the second piece. When you say there's wealth in equity, you've got way more money than he does. Tell me, how much way more do you have?

[Aaron]

Okay, he has about a half a million dollars in his retirement account and he has a home that has maybe a quarter million in equity. Okay, I have about a half million dollars in equity in my home and I have a million and a half dollars in retirement accounts and other investments and savings. And the other thing I mentioned is my parents are still alive, but I am going to inherit between 4 and 5 million dollars when they pass.

[Dawn]

This is one of the rare moments when I'm going to strongly recommend you walk in with a. And here's why. Let's say he's totally on the up and up. When there is four or five or six million dollar difference, then he's gonna have a cousin somewhere that thinks he just won the lottery or he's gonna have a parent or a kid. And, and I'm just telling you from years of doing the show, my fear is you're gonna walk out there, he's gonna sell his place, he's gonna move into your house, your parents are gonna pass away, and then if he disappears, he gets gonna take half of it. And so that would be my recommendation because there's such a gap there that you all sit down and discuss, hey, when my parents die, here's how this is going to go. And it's not to say you're not going to combine five.

[John]

I got to jump in real quick and ask you a question. Would you at least Recommend Premarital counseling? 1 million before we think prenup.

[Dawn]

I think you do premarital counseling before you do everything. Yes. Yeah.

[Aaron]

CHM isn't health insurance. It's a health cost sharing ministry. Check it out for [e-mail] budget.