"If you really love me"— Shark Tank star Mark Cuban’s White Castle date that led to 22 years of marriage

Love and relationships often hinge on moments of connection, sometimes in unexpected ways. For Shark Tank investor Mark Cuban, one such moment occurred before he married Tiffany Stewart. In an October 2024 interview with CNBC Make It, Cuban recalled a pivotal question he asked his wife, Tiffany Stewart:

“If you really love me, you’ll eat a White Castle burger.”

This simple yet meaningful gesture became a significant milestone in their relationship and marked the beginning of a marriage that has now lasted for over 22 years.

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How Shark Tank investor Mark Cuban’s White Castle test set the foundation for his long-lasting marriage

How Mark Cuban and Tiffany Stewart met

Mark Cuban met Tiffany Stewart in 1997 at a gym in Dallas. At that time, Cuban was already a successful entrepreneur, having sold his first company, MicroSolutions, for $6 million seven years earlier. In 1999, he became a billionaire by selling his second company, Broadcast.com, to Yahoo in an all-stock deal for $5.7 billion.

Meanwhile, Stewart was working in sales at an advertising agency, according to Forbes in 2000. Despite Cuban’s wealth, Stewart maintained a grounded perspective. In a New York Times profile, she remarked that she and Cuban still saw themselves as middle-class people. She described Cuban’s newly purchased Dallas mansion as “impractical,” reflecting her down-to-earth attitude.

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The White Castle date and its significance

Mark Cuban hails from a working-class family in Pittsburgh, where White Castle burgers were part of the regular diet during his formative years. In an episode of the Club Shay Shay podcast in October 2024, Cuban recalled sharing a piece of that early life with Stewart.

"We’re going to White Castle, and if you really love me, you’ll eat a White Castle burger. And she did,” he stated.

The significance of this moment extended beyond a simple meal. According to relationship expert Robert Wickham, Stewart’s willingness to participate likely resonated deeply with Cuban.

“He’s thinking, ‘OK, this person is in it for me. She wants to know me more,’” Wickham explained to CNBC Make It.

While eating a burger may not symbolize love universally, the Shark Tank investor viewed her response as a meaningful gesture of trust and acceptance.

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Marriage and family life

Mark Cuban and Tiffany Stewart got married on September 21, 2002, in Barbados after dating for five years. The wedding was private, with only 20 guests in attendance, making it a close friends-and-family affair.

Cuban and Stewart have three children: daughters Alexis and Alyssa and son Jake. The billionaire Shark Tank investor has been vocal about instilling values of responsibility in his children. In a 2020 interview with PEOPLE, Cuban stated:

“I'm not the dad that's like, 'Oh, you're mad at me? Let me buy you a Ferrari.’”

The Shark Tank fame added that his daughter would only receive a car like a Volvo, emphasizing the importance of earning rewards through effort. Cuban also shared his perspective on parenting during a 2021 appearance on The Ellen DeGeneres Show. He encouraged his children to pursue their passions, saying:

“The way to really be successful in my mind is just being able to get excited about something that you wake up every day looking forward to.”

In a 2023 interview on Hart to Heart, Cuban expressed pride in his youngest son, Jake.

“He’s hustling and selling stuff all the time,” Cuban said, referring to Jake as “a little me.”

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