The Ramsey Show – "You Can’t Win With Money When Your Relationships Are Messy"

Date: December 29, 2025
Hosts: Rachel Cruze & Jade Warshaw
Podcast Network: Ramsey Network

Episode Overview

This episode of The Ramsey Show dives into the ways financial issues are often entangled with messy or strained relationships—romantic, familial, or even professional. Through a series of live calls, Rachel Cruze and Jade Warshaw provide practical and direct advice on navigating debt, business struggles, financial boundaries with loved ones, and how life choices (like marriage, divorce, parenthood, and health challenges) impact financial peace. The underlying message is clear: transforming your finances requires both practical steps and honest conversations with yourself and those around you. “Normal is broke and common sense is weird,” Rachel emphasizes, championing a life of intentionality, sacrifice, and hope.

Key Discussion Points & Insights

1. Career, Business, and Debt Decisions

Segment: [00:59–08:42]
Caller: Miguel from Boston

• The Situation: Miguel, single, 147k in various debts, owns a first-year printing business; considering whether to sell the business for $30k or stick it out.
• Host Advice: Both hosts caution against making major changes out of desperation—don't immediately sell but also don't rely on a struggling side hustle as a full-time income. Find a full-time job for stability while keeping the business as a side gig.
  • Jade: "You're not on a living wage right now...this eats like a part-time side hustle." [03:40]
  • Rachel: “It’s tempting to hold tight for maybe six months...give yourself a time period. If you can’t grow it, sell the equipment, get the money and start fresh.” [06:30]
• Memorable Advice: Put a clear timeline on the experiment with the business; don’t take on more debt for it; up your income however you can (waiting tables, etc.); and focus on cash flow.

2. Dealing with Health-Related Financial Emergencies

Segment: [12:07–19:26]
Caller: Andrew from Cheyenne, Wyoming

• The Situation: On Baby Step 2, both Andrew and his wife seriously ill (mold exposure), considering a $10k–$30k experimental medical treatment not covered by insurance.
• Host Advice:
  • Avoid debt if possible for medical; pause the debt snowball and save aggressively for treatment. Try to negotiate costs, get close to the low end, and cash flow it even if it means delaying debt repayment.
  • Rachel: "Because it’s not a life or death... pause and save up for it." [19:10]
  • Jade: "Maybe one of you goes at a time to see if it’s helpful." [17:27]
• Key Insight: Using cash, even for medical, forces creative problem-solving and negotiation rather than just going further into debt.

3. Living Paycheck to Paycheck, Student Life, and Difficult Car Decisions

Segment: [21:29–30:25]
Caller: Sierra, Boone, North Carolina

• The Situation: Mid-20s couple with a child, husband earns ~$50k, Sierra is a full-time student aiming to be a marine biologist, living paycheck-to-paycheck after a hurricane set them back. They discovered they are $13k upside down on Sierra's $28k car.
• Host Advice:
  • Sell the expensive car—even if upside down—to cut the monthly payment, possibly sell the motorcycle too.
  • Recognize the temporary nature of financial hardship due to educational and family choices; hard “adult” decisions ahead.
  • Rachel: "Sell that car...I would rather have a $16,000 loan than a $28,000 loan." [27:26]
  • Jade: "Cutting up those credit cards." [29:36]

4. The Dangers of Cosigning and 'Relationship Debt'

Segment: [36:34–42:11]
Caller: Greg, Biloxi, Mississippi

• The Situation: Cosigned on an ex-fiancée’s $27k truck loan that’s now upside down.
• Host Advice: Encourage ex to sell the truck urgently; be prepared financially if she defaults since Greg is still liable.
  • Jade: “This is a tie to you...if it were different, you could make the argument for a clean break.” [38:04]
  • Rachel: “You’re in a tough position, Greg...You’re gonna be one of the sad examples.” [39:55]
• Key Point: Never cosign, even for someone you love (“Talk to Greg in Biloxi!”).

5. Massive Student Debt and Protecting Spousal Assets

Segment: [43:39–52:09]
Caller: Donna, San Antonio

• The Situation: Husband has $340k in student loans due to fraud, age 66, no assets; she’s 57, $1.4 million in investments.
• Host Advice:
  • Federal loans are not negotiable; consider using joint assets (possibly selling a property) to pay off if committed.
  • Address underlying relationship imbalances; the wealthier spouse shouldn’t feel solely responsible, but as a married team, there’s shared stewardship.
  • Jade: “There’s a balance of power here that feels off...work with someone to talk this through.” [51:06]

6. Navigating Divorce, Large Equity Payouts, and High Interest Loans

Segment: [65:36–73:54]
Caller: Wanda, Los Angeles

• The Situation: Must pay ex-husband $50k from home equity after divorce. Has $25k car loan, $12k 401k loan, high income but little savings.
• Host Advice:
  • Use a personal loan as last resort to avoid refinancing at much higher mortgage rates; set hard lines going forward (no more credit, 401k loans, etc.).
  • Jade: “It’s a blessing he dropped from $150k to $50k.” [71:29]
  • Rachel: “Draw that line in the sand...no more car payments, no more credit cards.” [72:13]

7. Financial Boundaries with Elderly Parents

Segment: [85:38–94:08]
Caller: Gabriel, Los Angeles

• The Situation: 72-year-old mom, nearly out of mortgage but no retirement savings, asking adult children for money, home worth $1.1M.
• Host Advice:
  • Advocate selling the house and downsizing to free up equity for investment and sustainable retirement spending.
  • The family must have a tough, unified conversation about boundaries and long-term solutions; continuing to “float” her is unsustainable.
  • Jade: “The math is not emotional...the more you float it, the more you’ll be doing it over the next 20 years.” [92:46]

8. Prenuptial Agreements & Uneven Asset Marriages

Segment: [96:07–104:38]
Caller: Derek, San Jose

• The Situation: Engaged, brings $12 million into marriage while fiancée has $50k; prenup discussion causing emotional friction.
• Host Advice:
  • A prenup is wise with such a disparity, but structure it graciously (e.g., everything after marriage is shared, only premarital assets protected in event of divorce).
  • Use therapy/counseling and transparent communication to keep the conversation healthy rather than adversarial.
  • Rachel: “You’re not being harsh, you sound gracious...I think it can feel like it’s all off to one side, but it’s really yours together unless you divorce.” [103:54]

9. Miscellaneous Quick Hits

• Saving for a Tiny House with No Credit Score: [105:56]
  • Don’t take on debt for tiny house; save cash, negotiate if buying used. [107:01]
• Should You Get a Master’s for a Slight Raise?: [111:03]
  • It’s not worth $18k in debt for a mere 2% income bump; only do it with cash. [112:28]
• Life After Divorce at 19: [76:51]
  • Take time, get good legal representation, and work out expectations with supportive parents before making hasty decisions.

Notable Quotes & Moments

• Rachel Cruz, on breaking financial cycles: “Normal is broke and common sense is weird.” [00:11]
• Jade Warshaw, on addressing income issues head-on: “The next line of defense is getting more income. That’s how it works.” [08:21]
• Rachel Cruz, to couple considering a car loan they can’t afford: “You can't afford this car, Brett. At $40,000, you can't afford half of your annual income going to the value of a car." [58:31]
• Jade Warshaw, on financial adulting: “You have to make different decisions if you want different results, Brett...Be weird!" [63:11, 63:13]
• Rachel Cruz, on peace: “We all want peace. Peace with our money, our homes, our schedules...” [08:42]
• Jade Warshaw, on the emotional challenge with prenups: “It's a tough way to start a marriage, because now we’re dividing yours vs. mine. Everything else in marriage is ‘we, us, ours’.” [102:55]
• Memorable call, Greg in Biloxi: Both hosts warn listeners to never cosign. “Talk to Greg in Biloxi!” [39:55]

Timestamps for Major Segments

• [00:59] Miguel – Business, debt, and tough choices
• [12:07] Andrew – Medical debt dilemma
• [21:29] Sierra – Living paycheck-to-paycheck and the car trap
• [36:34] Greg – The dangers of cosigning
• [43:39] Donna – Massive federal student loans in 2nd marriages
• [65:36] Wanda – Divorce, home equity, and restarting at 55
• [85:38] Gabriel – How to help aging parents without being the financial safety net
• [96:07] Derek – Navigating prenup emotions with a big asset gap

Final Reflections

Throughout the episode, Rachel and Jade return repeatedly to the theme that money management is inseparable from our relationships, both because those we love influence our spending, saving, and risk-taking habits, and because real peace with money must be built on clear expectations, boundaries, and a willingness to 'be weird.' The advice is tough but compassionate, rooted in both financial common sense and the messiness of relationships.

Rachel’s final encouragement:
"Take control of your money and create a life you love." [125:43]

This summary was crafted to reflect the episode’s authentic, conversational, and practical tone, giving non-listeners an actionable sense of the real issues, real people, and real hope that defines The Ramsey Show.