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Gates, 65, started dated software entrepreneur and venture capitalist Ann Winblad back in 1984, bonding over a shared interest in science.
Many of us never want to speak to our exes ever again, but after breaking up in 1987, Gates and Winblad managed to remain close friends, according to a 1997 Time magazine profile on the Microsoft co-founder.
In the piece, Walter Isaacson reports that when Gates married his wife in 1994, they had an agreement that meant he could continue to see Winblad, now 70, for an annual weekend getaway.
Referring to Winblad as one of 'Gates' vacation companions', Isaacson wrote: "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 were kindred minds as well as spirits."
Gates told Time he even consulted Winblad when he was considering proposing to his wife.
"When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval," he explained.
Winblad, who gave her blessing, added: "I said she'd be a good match for him because she had intellectual stamina."
Isaacson continued: "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."
Gates said of their trips: "We can play putt-putt while discussing biotechnology."
Winblad added: "We share our thoughts about the world and ourselves.
"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."
Bill and Melinda Gates announced that they were splitting up after 27 years of marriage earlier this week.
A statement said: "After a great deal of thought and a lot of work on our relationship, we have made the decision to end our marriage.
"Over the last 27 years, we have raised three incredible children and built a foundation that works all over the world to enable all people to lead healthy, productive lives.
"We continue to share a belief in that mission and will continue our work together at the foundation, but we no longer believe we can grow together as a couple in this next phase of our lives.
"We ask for space and privacy for our family as we begin to navigate this new life."
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