The Personal Finance Podcast
Episode: Money Expert Reacts to INSANE Reddit Finance Posts (AITA)
Host: Andrew Giancola
Guest/Co-Host: Irene
Date: November 19, 2025
Episode Overview
In this lively and insightful episode, Andrew Giancola dives headfirst into some of the wildest and most contentious personal finance stories sourced from Reddit’s "Am I The A**hole?" (AITA) community. Joined by his wife Irene, the duo reads and reacts to a series of real-life financial dilemmas—ranging from entangled romantic money issues to family and inheritance trouble. With sharp analysis, actionable takeaways, and relatable commentary, Andrew breaks down the dos and don’ts of handling money matters with loved ones.
Key Segments & Discussion Points
1. Should I Lend My Boyfriend Money for Taxes?
[02:37 – 06:03]
Reddit Scenario:
A woman refuses to lend her boyfriend $1,600 for overdue taxes after having already lent him rent money (never repaid) and regularly paying when they go out. He calls her "mean" and says she doesn't care about him.
Andrew’s Insights:
- Lending money repeatedly to someone who never pays it back is a "black hole."
- “You need to draw a line in the sand and you have to put your foot down unless you're willing to keep giving that person money and not expecting to get it back.” (Andrew, 04:17)
- Guilt trips and blame are red flags for financial irresponsibility.
- "Boundaries are a form of self-respect and not cruelty." (Andrew, 04:45)
Memorable Quote:
“If someone guilt you for not funding their irresponsibility, it's a sign—not a one-off moment—that you need to make sure that you're taking care of.”
— Andrew (05:01)
2. Yard Sale Ethics: Intervening for a Widow
[06:03 – 11:55]
Reddit Scenario:
A shopper at a yard sale advises a widow to reject a lowball $200 offer for valuable golf clubs, angering the would-be buyer but sparing her a big financial loss.
Andrew’s Insights:
- Flipping items for profit is fine, but “trying to rip off a widow is a different situation.”
- “If your profit depends on someone else’s ignorance, that’s not clever, that’s just shady.” (Andrew, 09:32)
- Always have valuable items appraised or researched before selling.
- Transparency should prevail: If flipping, at least be honest about your intentions and offer closer to fair value.
Memorable Quotes:
“But trying to rip off a widow is a different situation.”
— Andrew (08:55)
“If your profit depends on someone else’s ignorance, that’s not clever, that’s just shady.”
— Andrew (09:32)
3. Loaning Money to a Boyfriend in Debt
[11:55 – 17:26]
Reddit Scenario:
A woman regularly loans her boyfriend money (for food, etc.) as he pays off his credit card debt, but he never repays her. When she sets a boundary, he accuses her of being selfish.
Andrew’s Insights:
- If you lend money, expect not to get it back. If you must get it back, make that clear and enforce it.
- “Major manipulation” is at play, with guilt trips and emotional blackmail.
- Lending money reveals maturity gaps in relationships.
- Boundaries are necessary to protect trust, not a sign of coldness.
Key Takeaways:
- Lending money in a relationship exposes maturity gaps quickly.
- Guilt-tripping in response to boundaries is a serious red flag.
- Repeated broken promises with money signal larger issues.
Memorable Quote:
“Money in relationships exposes maturity gaps really fast... Boundaries don't make you cold or selfish, they protect your trust.”
— Andrew (15:24)
4. Gift Boundaries & Communication in Marriage
[17:26 – 20:38]
Reddit Scenario:
A woman asks her spouse not to buy her more board games/statues for her 40th birthday, but he takes offense and calls her ungrateful.
Andrew & Irene's Insights:
- Sharing gift preferences is practical and financially prudent.
- “If you're spending your hard earned dollars on someone else, you want to make sure two things. One, it is money well spent and two, the person actually likes and will use the item.” (Andrew, 18:48)
- Irene prefers clear communication—it reduces waste and friction.
Memorable Moments:
“Sometimes it's one less thing that I can take off my plate because you're telling me exactly what you want. So I like it.”
— Irene (20:18)
5. Setting College Tuition Boundaries with Children
[25:31 – 30:24]
Reddit Scenario:
A father tells his son he’ll pay for in-state college tuition but not more expensive out-of-state costs, which upsets the son.
Andrew’s Insights:
- “You are in no way, shape or form obligated to go into debt so that your kids can go to college.”
- Use the “oxygen mask method” (secure your retirement before funding extras like college tuition).
- Conversations about financial expectations for college should happen early, ideally before high school.
Memorable Quote:
“If you are not taking care of your own retirement, you should not pay a dime in your kids' college. Now we call this the oxygen mask method.”
— Andrew (27:23)
6. Old Money, Control, and Career Negotiations in Marriage
[31:01 – 36:39]
Reddit Scenario:
A high-earning woman is asked by her fiancé’s wealthy family to quit her job and be a stay-at-home mom, but they refuse her requests for legal or financial safeguards. She proposes a trust or prenup—sparking outrage.
Andrew’s Insights:
- Attempting to control a DIL’s (daughter-in-law's) career is problematic and outdated.
- Financial independence and legal protection are reasonable to request.
- Red flags: Control without backing, dismissing reasonable negotiation, misalignment of core values.
- “If someone’s trying to take away your financial independence, then you should negotiate protections 100%.” (Andrew, 36:03)
Memorable Quote:
“They want to control how she lives her life post marriage… That is something where, if you are, you know, an in law or you're someone in a situation, you should have zero say in what somebody does in their career unless they are not working.”
— Andrew (33:40)
7. Disclosing Past Lottery Winnings in a Relationship
[37:09 – End]
Reddit Scenario:
A woman’s boyfriend feels “deceived” after learning she paid off her house with lottery winnings instead of by “business savvy.” He questions her trustworthiness and advice.
Andrew’s Insights:
- There’s a difference between not disclosing personal history and active deception.
- Financial conversations reveal character—watch for red flags early.
- You don’t owe full financial disclosure early in relationships; entitlement to assets is a warning sign.
Key Takeaways:
- “Money will reveal character in a lot of situations.”
- “Don’t ignore early red flags… it’s going to get a lot, lot worse later on in the relationship.”
Memorable Quote:
“If you're not married, you have zero right to any of their money whatsoever… Getting mad at not having access to your assets is just absolutely crazy, especially when you're dating.”
— Andrew (39:32)
Notable Quotes Recap
- “If your profit depends on someone else’s ignorance, that’s not clever, that’s just shady.” (09:32)
- “Boundaries are a form of self-respect and not cruelty.” (04:45)
- “Money in relationships exposes maturity gaps really fast.” (15:24)
- “If you are not taking care of your own retirement, you should not pay a dime in your kids' college.” (27:23)
- “Don’t ignore early red flags with money… It’s going to get a lot, lot worse later on in the relationship.” (39:45)
Main Takeaways
- Red Flags Matter: Guilt-tripping, repeated borrowing, entitlement to someone else’s assets, and avoidance of financial boundaries are serious issues in all relationships.
- Boundaries Are Healthy: Setting clear limits—whether with family, partners, or even kids—protects you and is a mark of self-respect.
- Communication Is Key: Whether talking about gifts or college tuition, being direct saves money and prevents resentment.
- Financial Protection: If you’re being asked to give up earning power or take financial risks, always seek proper legal and financial safeguards.
- Transparency with Context: You don’t owe anyone your full financial history unless you’re at the right stage of commitment.
Listener Engagement
Andrew frequently encourages audience feedback and comments, particularly on contentious or relatable scenarios.
“Let us know in the comments down below on Spotify or YouTube what you think…” (Multiple segments)
Final Thoughts
This episode mixes sharp personal finance advice with practical relationship wisdom, all delivered in an approachable, conversational tone. The key thread is that boundaries, honesty, and education are essential for preventing money from ruining your closest relationships—no matter how wild the scenario.