U Up? Podcast: “Why Money Conversations Matter Early in Dating”

Guests: Jared Freid (Host), Vivian Tu (@yourrichbff)
Release Date: February 4, 2026

Episode Overview

This episode explores the importance of having money conversations early in dating and relationships. Special guest Vivian Tu—popularly known as @yourrichbff and author of "Well Endowed"—joins Jared Freid (filling in solo during Jordana Abraham's maternity leave) to dive into practical, emotional, and social issues around finances and partnership. The discussion ranges from splitting expenses and navigating socioeconomic differences, to the emotional baggage of bringing up money and its impact on modern dating.

Key Discussion Points & Insights

1. Vivian’s Background & Relationship Origin Story

(00:33–08:18)

• Vivian recaps her recent trip to Japan, noting generational travel trends and efficiency culture.
• She reflects on her own relationship: met husband at a work event via a mutual friend, reconnected six months later, did the “triple dipper” dating method (three dates in a row), and have now been together over eight years.
• Acknowledges how dating culture feels more toxic now, with more ghosting and lack of commitment, but Jared argues that the process has always been tough unless you find the right match.
• Notable Quote:
  • Jared: “As soon as you stop looking, it’s not difficult.” (07:56)
  • Vivian: “People aren’t actually taking the time to get to know people, which sucks.” (06:44)

2. Transitioning from Finance to Media

(11:24–15:24)

• Vivian details her move from Wall Street “desk” trading to a role in digital media (BuzzFeed), sparking her mission to educate coworkers and then a public audience on personal finance.
• She shares how mentorship from a successful female manager pushed her toward personal financial literacy.
• Notable Quote:
  • Vivian: “I want to make my money work really, really hard. I do not want to work very, very hard.” (15:16)

3. The Social Economy & Dating Networks

(16:28–20:00)

• Jared draws parallels between dating and outsourcing tasks (“the favors economy”), observing how technology has distanced us from the informal social networks that used to yield more setups/intros.
• both encourage singles to connect more deeply with married friends instead of relying just on apps or surface-level connections.
• Notable Quote:
  • Jared: “Go make the husband work for you... make him your ‘mailman’—he won’t set you up, but he might give you a green flag.” (17:10)

4. Main Topic: Money Conversations in Relationships

(22:35–41:04)

Email #1: Splitting Expenses with Unequal Incomes

(23:54–33:38)

• A listener asks about how to split rent and expenses with a partner who earns more. Vivian advocates for proportional splits, factoring in not only income but debts and family obligations.
• She describes how she and her now-husband negotiated their early living situation using prorated percentages.
• Notable Quotes:
  • Vivian: “Money in relationships is an art, not a science.” (24:37)
  • Vivian: “Talking over the proportional split is super helpful… Also consider debt, family obligations, and hidden wealth.” (27:10)

When to Talk About Money in Dating

(31:02–34:49)

• Vivian suggests bringing up financial values and goals through hypothetical, non-invasive questions (“If you inherited enough money to fund your life, what would you do?”).
• She argues early, casual questions are appropriate: “First date—just not tax returns, but dream-vacation questions.”

Can Socioeconomic Gaps Be Bridged in Dating?

(34:50–38:15)

• Both agree it can be very difficult for people from vastly different backgrounds to make it work long-term, especially if lifestyle or expectations diverge greatly.
• Vivian: “There is socioeconomic mobility, but dating ‘stratospherically’ up isn’t just rare—it’s hard to relate too.”
• Jared: “The dating advice is about telling you the weather, not changing the weather.”

Gender Roles and Perceptions of Money

(37:57–41:14)

• The hosts discuss how men are socialized to value their earning power, leading some to overemphasize salary as their major asset.
• Vivian: “If you’re dating a man and the only thing he brings to the table is money, you’re actually dating an incredibly poor person.” (38:15)

5. Games & Listener Scenarios

Ick or Picky: Bragging About Income on Early Dates

(41:30–46:47)

• Question: Is it an “ick” or just being picky if a man brings up being high-earning on date #1?
• Both agree: It’s off-putting and signals insecurity or lack of social skills. Talking salary too soon is “performative” and a turn-off unless logistics require it.
• Notable Quote:
  • Vivian: “They’re trying to make up for a lack of personality with stock options, and it’s not working.” (45:12)

When Should Salary Come Up?

(46:47–49:00)

• Vivian shares her personal example: it came up when a living arrangement forced a real conversation about logistics (after ~1 month, when their relationship was moving quickly).
• Key is transparency and context, not volunteering numbers “for no reason.”
• Jared: “Any time something’s said without being earned, it feels like manipulation.”

Red Flag or Dealbreaker: Prenup Requests

(49:28–53:28)

• Listener writes in: Is it a problem if a boyfriend brings up a prenup before engagement?
• Vivian: “This is a green flag—it’s just adult and practical. The government already has a default prenup for you if you don’t draft your own.”
• Both clarify: asking for a prenup isn’t about planning for divorce, but responsible planning—especially with family inheritances.

Red Flag or Dealbreaker: Pricey Third Date, Then Splitting

(53:42–57:45)

• Scenario: Partner chooses expensive restaurant, then asks to split.
• Vivian calls it a dealbreaker for lack of conscientiousness: “If you’re picking a pricey place, at least check if your date is comfortable footing half—you have to have empathy.”
• Jared agrees—finding it disingenuous and either tactless or opportunistic.

Notable Quotes & Memorable Moments

• “Money in relationships is an art, not a science.” – Vivian Tu (24:37)
• “Go make the mailman work for you.” – Jared Freid, using an analogy for leveraging social networks in dating (16:28)
• “If you’re dating a man and the only thing he brings to the table is money, you’re actually dating an incredibly poor person.” – Vivian Tu (38:15)
• “They’re trying to make up for a lack of personality with stock options, and it’s not working.” – Vivian Tu (45:12)
• “This is a green flag... The government already has a default prenup if you don’t draft your own.” – Vivian Tu, on prenups (50:28, 51:47)

Important Timestamps

• Vivian’s relationship history – 05:08–08:18
• Transition from Wall Street to personal finance education – 11:24–15:24
• Social economy & dating networks – 16:28–20:00
• Split expenses: Proportional vs. equal – 23:54–33:38
• Socioeconomic differences in dating – 34:50–38:15
• Gender, money, and dating – 37:57–41:14
• Men bragging about income: “Ick or picky?” – 41:30–46:47
• When to talk salary in dating – 46:47–49:00
• Prenup conversation – 49:28–53:28
• Pricey third date, splitsville – 53:42–57:45

Tone & Vibe

Conversational, candid, and occasionally irreverent. Both speakers weave in humor (as in describing high-end hotels or over-the-top finance bros) while remaining insightful and empathetic about the vulnerabilities people face in modern dating. Vivian balances research-based advice and real-life anecdotes; Jared grounds the talk in everyday dating realities.

Final Thoughts

The episode demystifies uncomfortable money talks in relationships with practical wisdom, humor, and an insistence on compassion and directness. Vivian’s “art, not science” framework empowers couples to have the right conversations based on their unique circumstances, while Jared reminds listeners that dating, like money, is rarely one-size-fits-all.

For more from Vivian Tu:

• @yourrichbff everywhere
• Book: “Well Endowed”

Contact:

• Submit questions: uup@betches.com
• IG: @u.up.podcast
• YouTube: Betches on YouTube