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

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.

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.

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]

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

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.

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.