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Mark Cuban recalls the weird test he put his wife through before marriage: "If you love me, you'll eat..."

Mark Cuban and Tiffany Stewart tied the knot in September 2002, but the Shark Tank judge reveals how he tested her love

Mark Cuban, the billionaire entrepreneur and star of 'Shark Tank', is no stranger to bold decisions in business and life. But before he decided to marry his now-wife, Tiffany Stewart, he set out to determine if she was truly "the one" by using some unconventional tests. By the time they started dating, Cuban had already made his fortune and wanted to make sure that their relationship was based on genuineness and love, not on wealth or status. In a candid interview on Shannon Sharpe’s 'The Club Shay Shay' podcast, Cuban opened up about some of the quirky ways he tested whether Tiffany was as down-to-earth as she appeared, including a trip to White Castle, among other things.

Taking someone on a date to a fast-food restaurant might seem unusual for a billionaire, but for Cuban, it was a deliberate choice. "I made her go to White Castle. That was the test before we got married!" Cuban joked. "I was like, 'We're going to White Castle, and if you really love me, you'll eat a White Castle burger!' She did." White Castle, known for its sliders, isn't exactly a luxury dining spot, but that was the point. Cuban wanted to see if Tiffany was genuinely interested in him as a person, not his wealth or lifestyle. Her ability to appreciate the simplicity of the gesture and enjoy the moment convinced him she was the real deal.

But Cuban’s tests didn’t end with fast food. In the same interview, he joked about another moment that tested their compatibility — something he called a "Dutch oven." In this context, "Dutch oven" refers to a playful prank where one partner farts in bed and then pulls the covers over the other’s head, trapping them under the blanket. Cuban joked that this too was part of the "test" — to see if Tiffany could handle his quick, dry wit. For him, even this lighthearted (and somewhat gross) moment showed their easygoing and genuine connection.

The couple first met at a Dallas gym in 1997, dated for several years, and married in a quiet, private ceremony in Barbados in 2002. Now with three children, they continue to keep much of their personal life under wraps.

Despite his $5.1 billion fortune, Cuban and Tiffany have remained refreshingly grounded in their everyday lives. Tiffany, a former advertising executive, drove a Honda and continued working even while dating Cuban. She once described their lifestyle as "middle-class people," showing that their relationship has always been rooted in shared values and humility.

To Cuban, it seemed rather simple- finding someone with the same view on life was worth more than any amount of money. "I just try to be the same person I was when I was broke," he said once. With Tiffany at his side, it certainly seems that he has found an ideal companion to keep him real, from the fast food chains to dealing with life under the hot spotlight.