Kevin O'Leary Says If You’re Dating, You’ll Want to Talk About Money on the 3rd Date — That’s How You’ll Know If There’s a Future

Kevin O'Leary Says If You’re Dating, You’ll Want to Talk About Money on the 3rd Date — That’s How You’ll Know If There’s a Future

Jeannine Mancini

Sat, August 22, 2026 at 11:01 PM GMT+3 5 min read

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First dates are for figuring out whether there's chemistry. The second can reveal whether the conversation survives dinner. By the third, "Shark Tank" investor Kevin O'Leary thinks it's time to find out whether the two people can actually build a life together — and that means talking about money.

In a clip posted by the "School of Hard Knocks" on TikTok in July, O'Leary was asked what dating advice he would give young entrepreneurs. O'Leary didn't recommend playing it cool. He said the third date is when the conversation should get serious.

"Three dates. It's how you start," O'Leary said. "Now on the third date, this is when you wanna get a couple bottles of wine because this is where the action really is gonna happen."

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He said that's when a couple should start exploring what a future together could look like.

"You want to explore what a future looks like together," O'Leary said. "You want to talk about money because the foundation of a successful relationship is economic."

He went even further, saying money can become a major problem in marriages several years in. His memorable conclusion was blunt.

"And money, honey," O'Leary said. "Your first child is actually money."

The Third Date Might Be Too Early — But the Money Question Isn't

Money isn't exactly a fringe relationship issue. A 2024 Ipsos survey found that 34% of partnered Americans said money was a source of conflict in their relationship. At the same time, 84% said they were on the same page financially, suggesting that talking about money doesn't necessarily mean a couple is doomed to fight over it.

Couples don't necessarily need to discuss net worth over the appetizer, but they probably shouldn't wait until after marriage to discover that one person is a saver and the other thinks every paycheck deserves a little celebration.

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Compatibility Has a Balance Sheet, Too

Financial compatibility doesn't mean two people need identical salaries or identical bank accounts.

It can mean agreeing on the basics. How much debt is acceptable? Is homeownership a priority? Should money be combined or kept partly separate? How much should go toward retirement, travel and investing? What happens when one person earns substantially more than the other?

Those questions can matter just as much as whether two people agree on where to live or whether pineapple belongs on pizza.

O'Leary's point is essentially that money reveals priorities. Two people can have great chemistry and still have very different ideas about what a successful life looks like.

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Building Wealth Doesn't Have To Wait for Marriage

Whether someone is single, dating or already married, having a financial plan of their own can make those conversations easier.

Real estate can be part of that plan without requiring someone to buy an entire rental property. Arrived allows investors to purchase fractional shares of rental properties for as little as $100, potentially giving them a share of rental income and property appreciation while Arrived handles the property management.

That isn't a substitute for building an emergency fund, paying down high-interest debt or investing through a diversified portfolio. But it gives people another way to participate in real estate without taking out a mortgage, becoming a landlord or waiting until they have enough money to buy an entire property.

O'Leary may be a little aggressive about putting money on the third-date agenda. But there's a useful idea underneath the theatrics.

Romance can start with chemistry. A lasting relationship probably needs a conversation about what happens when the check arrives.

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Building Wealth Across More Than Just the Market

Building a resilient portfolio means thinking beyond a single asset or market trend. Economic cycles shift, sectors rise and fall, and no one investment performs well in every environment. That's why many investors look to diversify with platforms that provide access to real estate, fixed-income opportunities, precious metals, and even self-directed retirement accounts. By spreading exposure across multiple asset classes, it becomes easier to manage risk, capture steady returns, and create long-term wealth that isn't tied to the fortunes of just one company or industry.

Arrived

Backed by Jeff Bezos, Arrived Homes makes real estate investing accessible with a low barrier to entry. Investors canbuy fractional shares of single-family rentals and vacation homes starting with as little as $100. This allows everyday investors to diversify into real estate, collect rental income, and build long-term wealth without needing to manage properties directly.

Frontieras

As electricity demand accelerates alongside AI and domestic energy production becomes a growing priority,Frontieras is developing patented technology that converts coal into fuels, chemicals, and low-emission energy products without combustion. Through its Regulation A offering, investors can gain exposure to an emerging energy infrastructure company focused on modernizing American industrial and power resources.

FarmTogether

Farmland has historically held its value through market volatility and delivered returns uncorrelated to stocks and bonds. For accredited investors,FarmTogether offers direct access to high-quality U.S. farmland starting at $15,000 — fully managed, with no landlord headaches.

Fundrise

Private real estate and private credit can add income and stability to a stock-heavy portfolio.Fundrise offers access to diversified private real estate and credit strategies through an easy-to-use platform, with professionally managed portfolios designed to generate passive income and long-term growth.

Qnetic

As electricity demand rises alongside AI, data centers, and renewable energy, long-duration energy storage is becoming increasingly important.Qnetic is developing a kinetic energy storage system designed to provide long-lasting, chemical-free electricity storage, offering investors exposure to the infrastructure supporting a more resilient and reliable power grid.

Mode Mobile

Mode Mobile is changing the way people interact with their phones by letting users earn money from the same apps and activities they already use every day. Instead of platforms keeping all the advertising revenue, Mode Mobile shares a portion back with users who engage with content, play games, and scroll on their devices. Named one of Deloitte's fastest-growing software companies in North America, the company has built a large beta user base and is scaling a model that turns everyday smartphone usage into a potential income stream.

EquityMultiple

For accredited investors looking beyond stocks and bonds, EquityMultiple provides access to vetted commercial real estate deals starting at $5,000, with only ~5% of opportunities passing their due diligence process.

BluSky AI

As artificial intelligence drives unprecedented demand for computing power, the infrastructure behind it is becoming just as important as the software itself. BluSky AI is developing modular, prefabricated data centers designed to bring AI compute capacity online faster than traditional builds, giving investors exposure to a critical layer of the rapidly expanding AI ecosystem through its Regulation A offering.

Image: Imagn

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