Her Boyfriend Is Afraid Getting Married Would Complicate Their Finances

Summary

Podcast Summary: The Ramsey Show Highlights

Episode: Her Boyfriend Is Afraid Getting Married Would Complicate Their Finances
Date: December 24, 2025
Host: Dave Ramsey (with Rachel Cruze)
Duration: ~10 minutes

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Overview

In this episode, Dave Ramsey and Rachel Cruze address tough questions from listeners about relationships, marriage, and managing finances amidst life changes. The episode is split between two central calls: the first from a woman facing a crossroads in her relationship due to her boyfriend's aversion to marriage (main segment), and the second from a listener seeking advice on whether to sell an Airbnb property following a job loss.

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Main Discussion: Relationship & Marriage Fears

[00:06 - 05:25]

Key Points

• Caller’s Situation

  • Caller (woman, 53) has been dating her boyfriend for two years; both are financially stable and nearly debt-free.
  • The boyfriend, who was deeply hurt by a past marriage (20+ years ago), is firmly against marrying again.
  • The caller was initially hopeful she could change his mind but is now facing the reality of their differing expectations.

• Emotional Dynamics

  • Dave pinpoints the boyfriend's resistance as stemming from unresolved emotional scars:

    “He still lives in that.” – Dave Ramsey [00:37] "All marriages are not bad. All people don’t mistreat each other the way she did. And so his conclusion is ill founded... he’s unwilling to address it.” – Dave Ramsey [01:55]

  • Rachel emphasizes the problem with trying to persuade someone into marriage:

    “I wouldn't want to have to convince somebody of it... even if he decided, okay, I'll marry you, that doesn't feel good either, does it?” – Rachel Cruze [02:13]

  • The hosts counsel the caller to accept their mismatched values:

    “You've been dating for two years and you figured out it’s not a match. And so you start.” – Dave Ramsey [03:15]

• On Healing and Moving Forward

  • Dave suggests that the boyfriend needs therapy or pastoral counseling to work through old wounds:

    "If he was on the phone, I would tell him to sit down with a therapist... start reaching towards some healing from his past. Because he's hurting. The scars are dominating his thought pattern rather than his bright future. And he's about to lose a great gal because of it." – Dave Ramsey [03:32]

  • Rachel asks if the caller has ever suggested this to her boyfriend, but the caller has not.

• The Issue of Commitment

  • The boyfriend previously had a long-term relationship after his marriage where no formal commitment was required; when it ended, he viewed the lack of legal involvement as a positive.
  • The caller disagrees, wanting the security and commitment of marriage:

    “But that’s not the commitment I want.” – Caller 1 [04:42]

• Hosts’ Closing Thoughts

  • Rachel and Dave recognize the boyfriend’s honesty but note that it doesn't make the reality any easier and encourage having these conversations early:

    “You have these conversations early and often and he did say it. He said it from the beginning.” – Rachel Cruze [04:58]

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Notable Quotes & Moments

• On Playing the Waiting Game:

  "I was hoping you were going to just give me some magic to convince him... But I'm kind of — I think it is good and I think it's him." – Caller 1 & Dave Ramsey [03:25–03:32]

• Dave on Heartache:

  "Because the heartbreak is more extreme the further you’re into it, so. Ouch. Ouch.” – Dave Ramsey [05:10]

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Second Discussion: Should We Sell Our Airbnb?

[05:31 - 09:50]

Key Points

• Caller’s Situation

  • Second caller ("Lynn") lost her job and is considering selling an Airbnb property for financial stability.
  • Her husband earns $37k at a local supermarket after leaving his own business; previously, the family relied on the caller’s $90k income as an executive admin.
  • Job prospects in South Carolina for similar positions pay around $40-50k, lower than she earned in Pittsburgh.

• Financial Snapshot

  • The Airbnb is valued at $200k; they owe $112k on it.
  • Family moved south to be closer to their daughters and grandchildren.

• Ramsey’s Advice

  • Dave recommends selling the Airbnb to create a financial buffer during the job search:

    “To answer your question simply, yes, I would sell it.” – Dave Ramsey [08:25]

  • He challenges the caller’s assumption that she can only earn less in her new location, suggesting she look in larger nearby markets like Charlotte and rethink her mindset:

    “It is...interesting observation, 30 years of doing this, that people, when they lose a job for some reason, always assume they're going to make less. They never assume it's an opportunity to make more. I don't know why that is.” – Dave Ramsey [09:23] “Columbia is not a huge, huge market, but it's big enough...I think it’s just a belief system...” – Dave Ramsey [09:35]

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Timed Highlights

• The Core Relationship Issue – [00:10-01:55]
• Rachel’s Perspective on ‘Convincing’ a Partner – [02:06-02:26]
• Caller Shares Boyfriend’s Past Relationships – [04:01-04:44]
• Hosts’ Summing Up on Moving Forward – [04:54-05:25]
• Second Caller’s Airbnb Situation – [05:36-08:25]
• Dave’s Broader Career & Mindset Advice – [08:25-09:35]

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Tone and Style

The tone is candid, empathetic, and direct. Both Dave and Rachel offer tough love, practical advice, and empathetic support while urging callers to recognize their worth, set boundaries, and act in their own best interests both emotionally and financially.

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Takeaways for Listeners

• Personal relationships: Don't enter partnerships hoping to change someone’s core values or beliefs about commitment.
• Emotional health: Address old wounds—through counseling if necessary—so past trauma doesn't limit future possibilities.
• Financial transitions: Reassess assumptions during job changes; sometimes the perceived limits are self-imposed.
• Action over inaction: Sometimes the healthiest, wisest move is the hardest emotionally, but it’s necessary for personal well-being and growth.

Transcript

[Dave Ramsey]

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[Caller 1]

I'm 53 years old. I've been dating my boyfriend for about two years now. And the idea of long term commitment in marriage has been coming up. We're both financially stable, no debt, significant amount in retirement accounts, and he is just straight up against marriage.

[Dave Ramsey]

He got burned bad before, didn't he?

[Caller 1]

Did he actually. He really got burned bad. And that was, I mean, that was 20 years ago. 25 years ago.

[Dave Ramsey]

Yeah. But he still lives in that.

[Caller 1]

Yes.

[Rachel Cruze]

Was he upfront about that? Has he been upfront about the fact that he doesn't want to be married?

[Caller 1]

Yes.

[Rachel Cruze]

And you were thinking maybe you could change his mind?

[Caller 1]

I thought I was.

[Caller 2]

Okay.

[Caller 1]

And now I'm like. But it's not. I mean, I understand. We both, like, we both have kids.

[Dave Ramsey]

Yeah.

[Caller 1]

They're almost all adults. We both are financially stable.

[Dave Ramsey]

That's so hard.

[Caller 1]

And obviously it is.

[Dave Ramsey]

Yeah. I'm sorry.

[Caller 1]

So I'm just stuck, right?

[Rachel Cruze]

No, you're. I mean, you're not stuck.

[Dave Ramsey]

You're not stuck. You've already. You've already decided who you are. And he decided who he is, and that's a bad thing. I'm sorry. Yeah.

[Caller 1]

You know, it didn't feel bad.

[Dave Ramsey]

I thought. I wish it didn't feel bad, too, but it feels awful. It hurts because you really. I mean, you like the guy, obviously, might even say love the guy. But I would just say, you know, I thought I could be okay not being married, and I'm not okay. And you're not okay talking about getting married, even, or getting counseling for what happened to you. I'm not her. And I feel like she's being held against me and against the institution of marriage. All. Marriage is not bad. All relationships are hard, including marriage. But all. All marriages are not bad. All people don't mistreat each other the way she did. And so his conclusion is ill founded. It's based in scars and pain, and he's unwilling to address it.

[Rachel Cruze]

And here's the other part of it, Kelly. And I'm thinking about this just from. If I were in your shoes, I wouldn't want to have to convince somebody of it.

[Dave Ramsey]

Yeah.

[Rachel Cruze]

Do you see what I'm saying? Even if you laid out some sort of a, hey, if you don't do this, I'm walking. And. And then if he decided, okay, I'll marry you, that doesn't feel good either, does it?

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[Caller 1]

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[Caller 1]

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[Caller 1]

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[Rachel Cruze]

That doesn't feel good either, does it?

[Caller 2]

No, it doesn't.

[Caller 1]

It doesn't because I've thought about that.

[Rachel Cruze]

You know, that's the tough part. It's tough. I'm not going to lie. I. I feel for you.

[Dave Ramsey]

I'm sorry.

[Caller 1]

And it's, it's. It's a few years in the future still, but I don't know, I'm. I'm not 20. Well, I mean, you've already want to waste those years.

[Rachel Cruze]

Did you say three years?

[Dave Ramsey]

I wouldn't. No, there's no, there's no few. There's no, no time in the future. It's. You've been dating for two years and you figured out it's not a match. And so you start.

[Caller 1]

All right. I was hoping you were going to just give me some magic to convince him that it was, that it was good.

[Dave Ramsey]

But I'm kind of. I think it is good and I think it's him. I think if I were for, if I, if he was on the phone, I would tell him to sit down with a therapist, sit down this pastor and start reaching towards some healing from his past. Because he's hurting. The scars are dominating his thought pattern rather than his bright future. And he's about to lose a great gal because of it.

[Rachel Cruze]

Have you mentioned that to him, that maybe there's some healing that needs to take place?

[Caller 1]

No, I don't think I've ever actually said those words. He had a long term partner who didn't require marriage, and I think he just kind of settled into that and then they broke up very easily.

[Caller 2]

Right.

[Caller 1]

I mean, it was, hey, let's go our separate way.

[Rachel Cruze]

So he's never been actually married before?

[Caller 1]

No, no, he was married and then.

[Dave Ramsey]

And then he had long term.

[Rachel Cruze]

Got it.

[Caller 1]

And then he had a long term relationship that she didn't require him to marry. And then she just kind of said, okay, I'm out. I'll see you. And he was like, oh, okay. And he's like, see, I didn't have to go through a divorce. I didn't have to pay a lawyer. This is great. This was so wonderful. And I'm like. But that's not the commitment I want.

[Dave Ramsey]

Yeah. Yeah, that's exactly right. This is. Yeah. I'm sorry.

[Rachel Cruze]

Yeah.

[Caller 2]

Yeah.

[Caller 1]

All right. Well, I appreciate you taking my call.

[Rachel Cruze]

I'm sorry.

[Dave Ramsey]

Thanks. Thanks for calling.

[Rachel Cruze]

Oh, that's tough.

[Dave Ramsey]

So that is hard. It's hard.

[Rachel Cruze]

That's. That's tough. It's. You have these conversations early and often and he did say it. He said it from the beginning.

[Dave Ramsey]

Yeah. I mean, he can't argue with a guy in terms of his honesty, but that still doesn't. It's just not a matter.

[Rachel Cruze]

Painful.

[Dave Ramsey]

Yeah. I think the thing is, the only thing I might have done if I. Looking back on it, I'm trying to look backward on this is maybe, you know, a little sooner in the. Rather than investing two years and. Because the heartbreak is more extreme the further you're into it, so. Ouch. Ouch. Lynn is in Columbia, South Carolina. Hey, Lynn, what's up?

[Caller 2]

Hey. Thank you for taking my call.

[Dave Ramsey]

Sure. How can we help?

[Caller 2]

I would love. We would love your opinion on if it makes sense in the current housing market to sell our Airbnb.

[Rachel Cruze]

Tell us more. Why are you thinking of selling?

[Caller 2]

So I lost my job. My position was eliminated about six weeks ago and I'm currently looking for another job. But if it doesn't, I don't think I'm going to be able to make as much as I was. So if it doesn't work out, we would definitely have a profit from selling the Airbnb and we could definitely live on that for a while.

[Dave Ramsey]

Does your husband work?

[Caller 2]

He does.

[Dave Ramsey]

And what does he make?

[Caller 2]

He probably makes only about 37 a year. And let me explain, because he, he had a business. We moved into South Carolina about a year ago. He. He had a business, a distributing business. And we were living on, mostly on my income because I was at a company for a very long time and they told me that, you know, it would work remotely and regardless, they did eliminate my position. So he's working at a local supermarket in a receiving area. And what were you making for a higher paying job? I was making probably 90.

[Dave Ramsey]

Doing what?

[Caller 2]

I was an executive admin to a president of a company.

[Rachel Cruze]

Now what made you say that? You probably won't make that again. That's a crazy statement.

[Caller 2]

Because in South Carolina I was a. I did that my entire life. And just, just step into a position, an executive admin position. You're not. I'm not going to. There's Nothing available currently here that I've looked at in the last six weeks. Two months. That starts at that level.

[Rachel Cruze]

Understood. What do they start at?

[Caller 2]

More 40, 50.

[Rachel Cruze]

Interesting. Okay, back to the Airbnb for a second. What's it worth?

[Caller 2]

Probably 200.

[Rachel Cruze]

And what do you owe on it?

[Caller 2]

112.

[Dave Ramsey]

Where were you living before?

[Caller 2]

So in Pittsburgh, is that what you mean?

[Dave Ramsey]

Yeah. And why did you choose South Carolina?

[Caller 2]

Two of our three daughters live around the corner from us, and one was in Charlotte, so we needed to be near them and near our grandchildren.

[Rachel Cruze]

Is Airbnb in Pittsburgh?

[Caller 2]

No. So we bought it in 2020 so that I could come down here and work and be close to the grandkids when I came down. And then when we moved down here last year, we decided to Airbnb. Well, actually decided to Airbnb.

[Dave Ramsey]

To answer your question simply, yes, I would sell it.

[Rachel Cruze]

Okay.

[Dave Ramsey]

But then the other. The other thing I want to address is, number one, your husband needs a different position, and number two, your set of assumptions. I, frankly, I'm very familiar with Columbia and I'm very familiar with Charlotte, and I'm frankly shocked that you haven't seen any executive positions anywhere. Assistant positions over 40 or $50,000. That's. I know if you go to Charlotte, you would. And that might be your. Well, that's where one of the other kids lives. I heard that. And so you'd be an hour and a half from your grandkid over on that side, but be next to the kid that's in Charlotte. So if you need the income. But I don't know what you all need to make to survive and so forth, but on the back end of your career. But I. It is a. It's an interesting observation, 30 years of doing this, that people, when they lose a job for some reason, always assume they're going to make less. They never assume it's an opportunity to make more. I don't know why that is.

[Rachel Cruze]

We've had all those years of experience.

[Dave Ramsey]

I would think now Columbia is not a huge, huge market, but it's big enough that there ought to be somebody over 40 playing for an executive assistant. That doesn't feel right. So. But I think it's just a belief system. You just like, oh, I'm always going to make less because I'm not in Pittsburgh. Well, I mean, that's pretty snobbish. So South Carolina doesn't pay what Pittsburgh pays. Yes, they do. So, hello. Create your free every dollar budget today. The simplest way to budget for your life.