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, a Shark Tank investor, believes that the third date is when couples should start discussing money to determine if there is a future together. In a TikTok clip, O'Leary advised young entrepreneurs not to play it cool on the third date and to instead explore what a future together could look like. He emphasized that talking about money is crucial as it forms the foundation of a successful relationship.

O'Leary noted that money can become a significant problem in marriages several years down the line. According to a 2024 Ipsos survey, 34% of partnered Americans reported money as a source of conflict in their relationship, while 84% said they were financially compatible with their partners. However, O'Leary highlighted that financial compatibility doesn't mean identical salaries or bank accounts; it involves agreeing on basic financial matters such as acceptable debt levels, homeownership priorities, and retirement contributions.

He suggested that couples can participate in real estate investing through platforms like Arrived Homes, which allows investors to buy fractional shares of rental properties for as little as $100. This option provides an opportunity to diversify into real estate without the need for property management or large investments.