Podcast Summary: The JTrain Podcast – "How Couples Should Talk About Money"

Host: Jared Freid
Guest: Ashley Feinstein Gersley (The Fiscal Femme)
Date: October 8, 2025
Episode Type: Chit Chat Wednesday – Relationships & Finance

Episode Overview

This episode of The JTrain Podcast focuses on how couples should talk about money, featuring certified financial planner, author, and financial educator Ashley Feinstein Gersley, also known as The Fiscal Femme. Jared and Ashley delve into the anxieties, challenges, and practical steps couples—and friends—can take to improve communication around money in relationships. The duo take on common scenarios, share actionable insights, and answer listener emails about money issues in dating, relationships, and group travel.

Key Discussion Points & Insights

1. Making Finance Approachable and Sexy

• Naming the Brand (Fiscal Femme):
  • Jared jokes about the "naughty" vibe of "Fiscal Femme" (01:26), to which Ashley explains it came from wanting a woman-focused, approachable blog name.

  "I basically was sharing about my own money journey, trying to come up with a name for the blog...one of my friends spoke French and she said femme meant woman. And so I'm like, oh, the fiscal woman. But it has the alliteration." — Ashley (01:53)

• Ashley emphasizes the importance of demystifying and destigmatizing money talk, making it palatable and inclusive rather than intimidating or overly technical.

2. Financial Credentials: Do They Matter?

• Ashley explains her path to becoming a CFP (Certified Financial Planner), initially resisting credentials to seem more relatable, but later seeing the value of the certification as a sign of trust and fiduciary responsibility.

  "For a long time, it was based on just my experience...I think it's important with finance to understand where the incentives are and how people are getting paid." — Ashley (04:00)

3. The Biggest Money Issue in Relationships

• Ashley identifies "financial polarization" as a major problem: partners become exaggerated versions of their saver or spender tendencies when in a relationship.
• She introduces the idea of “money parties” as a fun, regular, judgment-free check-in about shared finances.

  "Even if we might be similar, like a saver and a saver or a spender and a spender, when we get together, the saver becomes more savvy, the spender becomes more spendy, and it creates stress in the relationship." — Ashley (05:05)

4. The Money Party: How, When, and Why

• How to Host:
  • Set aside a regular time (monthly is suggested), make it enjoyable (playlists, tea, pajamas), and keep an open, non-judgmental tone.
  • Review spending, check in on goals, discuss joint expenses.
• When to Start:
  • Start money conversations when shared expenses appear (e.g., planning a trip or attending a wedding together).
  • Use upcoming shared financial decisions as a natural segue.

  "The money party essentially is setting aside time...I make them fun. I have a playlist with songs that pump me up about money. I'm happy to share it." — Ashley (06:29)

• How to Bring It Up:

  "Hey, we're going to a wedding next month. This is our first trip together. There's going to be money stuff going on. I just heard this podcast where they talked about a money party. Would you be up for that?" — Jared (11:05, paraphrased question)

5. Easing Into Money Talk (Not Full Disclosure Immediately)

• Begin with budgeting for shared events, values, or family backgrounds instead of “full financial nudity.”

  "We don't need to, like, show them our balances...you can wade into that slowly...it's more like, hey, how are we going to divide the expenses for the wedding?" — Ashley (11:57)

6. Red Flags & Relationship Dynamics

• Money Red Flags:
  • Unwillingness to discuss money or improve
  • Using money manipulatively or to control
• Openness to learning is more important than current situation (e.g., low credit score is not a dealbreaker if there's willingness to address it).

  "If someone's...making you feel stupid about talking about money, I think those are red flags, like the way you're able to communicate about it." — Ashley (16:18)

7. The Number One Money Fight: Different Valuations

• Most common argument: Disagreements over what to spend on and different values (experiences vs. things, convenience vs. thrift).

  "My husband and I, he like values buying things. I value experiences...When do you pay to make things more convenient and when do you do it yourself and save money?" — Ashley (17:25)

• Jared notes how partners call out each other's financial hypocrisies, leading to embarrassment or defensiveness.

8. Structuring Shared Finances

• Options range from fully combined accounts to strictly separate (with Venmo/transfer for expenses), but most couples do a mix.
• Setting agreed contributions (equal or proportional to income) and maintaining individual "no-judgment" spending money pools are recommended.

  "Somewhere in between is where I've seen the most common and the most success...the key is talking about it. And if there is stress or something that feels like it's not working...speaking up and trying to adjust the system." — Ashley (27:50)

9. Listener Emails: Real-Life Scenarios

Email 1: "Does My Husband Owe Me Money?" (35:47)

• Scenario: Married couple with separate finances, returning from a family trip with leftover cash from his parents. Husband keeps and spends the cash without discussing, leading to feelings of unfairness.
• Ashley’s Response:
  • She notes that fully separate finances increase admin burden and can create resentment and power imbalances, especially when one partner is the default “manager” for kid-related expenses.
  • She advocates for re-examining the “tit-for-tat” dynamic and moving toward more joint decision-making, especially concerning shared children and household needs.

  "I do see how much admin there is to keep this completely separate...when they've commingled things, they're, they're joint assets. But I do think the third, the child...should be separate from their expenses if we're doing like completely tit for tat." — Ashley (37:43)

Email 2: Bachelorette Party Planning & Collecting Money (43:12)

• Scenario: Listener wants tips on fairly managing lodging costs and collections for a group bachelorette.
• Advice:
  • Always collect money before booking or paying for group expenses.
  • Create transparency: present a few price-tiered options up front, get group input, require deposits to confirm attendance.
  • Outline expected costs in detail so no one is surprised or feels taken advantage of.

  "Giving a couple options even, or having an idea of what you want and saying it'll be this much per person, ish. Are you in?" — Ashley (44:35) "Every good bachelor party I've gone on had a great itinerary and was a lot of work for someone...if you give people three options, the expectations set, and then you vote on it as a group." — Jared (44:35)

10. Money Stories, Fears, and Compassion

• Sharing first money memories and biggest financial fears helps partners understand each other's “money psychology.”

  "If your partner understands where that's coming from, they can have more compassion than if it's just like, why are you so stingy with these things?" — Ashley (20:08)

• Jared relates how his own family dynamics and career instability shape his financial fears and relationship anxieties.

11. Financial Abuse & Infidelity

• Ashley explains financial abuse as restricting access to funds, using money to control, or saddling partners with debt.
  • 99% of domestic violence cases include financial abuse.
• Financial infidelity (lying about money) is also a significant relationship threat. (24:44–26:37)

12. Transparency vs. Privacy: Business Owners and Nontraditional Income

• Jared discusses how, as a comic and business owner, nontraditional/freelance careers add extra layers of complication, disclosure, and insecurity in couple finances. (31:37–33:39)

13. New Fiscal Femme Initiative: "How Do You Afford This?"

• Ashley teases her next project, interviewing real people about how they afford everything from rent to gifts—for more transparency and less comparison.

Notable Quotes & Memorable Moments

• “Communication is so important because an understanding where the other person is coming to the money party when it comes.” — Ashley (05:50)
• “It would be, I would have to say so much more out loud than I normally have to say, if that makes any sense.” — Jared (29:51)
• “If someone's...making you feel stupid about talking about money, I think those are red flags...”— Ashley (16:18)
• “How many nice dinners do we want to go on have on this vacation?...there's compromise always because we're going to disagree...” — Ashley (41:07)
• “We should go to these influencers and just be like, walk us through this...I can tell you there's a lot of influencers that would not go on that show.” — Jared (50:55)

Timestamps for Important Segments

| Timestamp | Topic | |-----------|-------| | 01:26 | Origin of "Fiscal Femme" & financial sexiness | | 03:02 | Should only CFPs give advice? Credentials and approachability | | 05:05 | Polarization in couples + the "money party" ritual | | 06:29 | Guidelines for starting money conversations in relationships | | 11:05 | How to bring up a money party before shared expenses | | 16:18 | Money red flags in dating | | 17:25 | Most common money fights in couples | | 27:50 | Structuring shared/joint finances | | 35:47 | Listener email: Does my husband owe me money? (Portugal trip scenario) | | 43:12 | Listener email: Collecting & managing money for bachelorette parties | | 50:11 | Ashley introduces "How Do You Afford This?" project |

Actionable Takeaways

• Host regular “money parties” with your partner or friends for low-pressure, proactive financial check-ins.
• Start money conversations early—use upcoming shared expenses as an opening.
• Don’t wait for resentment: Build systems for fair contributions, flexibility, and small personal spending pools.
• For group travel/events, collect money before booking, and communicate costs and options clearly.
• Understand your partner’s (or your own) money history—first memories, biggest fears—and practice compassion.
• Address financial red flags early: communication, openness to learning, and mutual respect are paramount.

Closing

Jared and Ashley keep the discussion light, relatable, and actionable, making the daunting topic of shared finances and money conversations feel accessible and even fun. Whether you’re dating, cohabiting, or planning group trips, this episode offers frameworks and empathy to improve how you think and talk about money.

Follow Ashley: @thefiscalfemme
Check out her books: Financial Adulting, The 30-Day Money Cleanse
Watch for her new project: "How Do You Afford This?"