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

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.

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]

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]

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]

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]

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.

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.