It's not every day you hear about a billionaire spending a weekend at the beach with his ex — and having his wife's full blessing. But that's exactly what Bill Gates arranged before marrying Melinda French in 1994.
According to a Time magazine profile written by Walter Isaacson in 1997, Gates had a unique agreement with Melinda: he could spend one long weekend each spring with his ex-girlfriend, software entrepreneur and venture capitalist Ann Winblad, at her beach cottage on the Outer Banks of North Carolina.
The getaway spot, reportedly a cozy four-bedroom oceanfront house in Corolla called "Castle Sween," became a tradition. "Every spring, as they have for more than a decade, Gates spends a long weekend with Winblad at her beach cottage… where they ride dune buggies, hang-glide and walk on the beach," Isaacson wrote.
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It wasn't exactly scandalous in tone — but it was certainly unconventional. Especially considering what they did there.
"We can play putt-putt while discussing biotechnology," Gates told Isaacson.
Winblad, for her part, described their time together in more poetic terms: "We share our thoughts about the world and ourselves," she said. "And we marvel about how, as two young overachievers, we began a great adventure on the fringes of a little-known industry and it landed us at the center of an amazing universe."
The relationship between Gates and Winblad began in the 1980s after they met at a computer conference. According to the same Time profile, they once went on "virtual dates" by driving to the same movie in different cities and discussing it on their cell phones. Winblad even convinced him to go vegetarian for a while — a phase he "resolutely abandoned."
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They dated exclusively from 1984 until 1987, when they broke up "partly because Winblad, five years older, was more ready for marriage," the article said. Despite the breakup, the bond remained.
So strong, in fact, that Gates sought Winblad's opinion before proposing to Melinda. "When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval," he said. Winblad gave it, later saying, "I said she'd be a good match for him because she had intellectual stamina."
While the setup might seem cartoonish by today's standards — one of the world's richest men retreating to the beach with his ex to hit mini golf balls and talk about gene therapy — Gates presented it as a matter of mutual respect and friendship. Melinda, according to Gates, approved of the arrangement.
Still, the public fascination with the annual rendezvous resurfaced when the couple announced their divorce in 2021, prompting many to revisit the odd clause in one of the world's most high-profile marriages.
As for the cottage, the beach, and the putt-putt? That's all part of the legacy too. Just another reminder that even in the most data-driven marriages, there's always room for a little emotional code — as long as everyone signs off on the terms.
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