Bill Gates Took Yearly Beach Vacations With This Ex Throughout His Marriage to Melinda Gates

There are many aspects of Bill Gates and Melinda Gates’ marriage that we will likely never understand as they separate after 27 years together, a development announced earlier this week by the ex-couple on Twitter. But one particularly unusual detail about the tech billionaire’s union gained interest today after a 1997 Time profile resurfaced in which his relationship with longtime ex-girlfriend Ann Winblad was discussed in some depth, including the extent to which they remained involved after his marriage to Melinda. Per the article, Gates and Winblad continued to spend a long weekend on the beach together once a year even after he married Melinda in 1994 — and it seems to have been an agreed-upon dynamic with Melinda.

Time‘s Walter Isaacson wrote a profile on Bill Gates’ personality and close relationship in 1997 in which Winblad, and his arrangement with Melinda, are clearly outlined.

“Another of Gates’ vacation companions is Ann Winblad, the software entrepreneur and venture capitalist he dated during the 1980s,” Isaacson writes. “They met in 1984 at a Ben Rosen-Esther Dyson computer conference and started going on ‘virtual dates’ by driving to the same movie at the same time in different cities and discussing it on their cell phones. For a few years she even persuaded him to stop eating meat, an experiment he has since resolutely abandoned.”

“They broke up in 1987, partly because Winblad, five years older, was more ready for marriage,” the article continues. “But they remain close friends. ‘When I was off on my own thinking about marrying Melinda,’ Gates says, ‘I called Ann and asked for her approval.’ She gave it. ‘I said she’d be a good match for him because she had intellectual stamina.’ Even now, Gates has an arrangement with his wife that he and Winblad can keep one vacation tradition alive. Every spring, as they have for more than a decade, Gates spends a long weekend with Winblad at her beach cottage on the Outer Banks of North Carolina, where they ride dune buggies, hang-glide and walk on the beach.”