Why did Bill Gates split with Ann Winblad? Billionaire sought ex-flame's approval before proposing to Melinda

Ann Winblad thought Melinda would 'be a good match for him because she had intellectual stamina'

                            Why did Bill Gates split with Ann Winblad? Billionaire sought ex-flame's approval before proposing to Melinda
Bill Gates asked for Ann Winblad's approval before marrying Melinda Gates (Getty Images)

Fueling the speculation surrounding the possible reason Bill and Melinda Gates decided to call it quits on their 27-year-old marriage, it has been recently reported that Microsoft co-founder asked his ex-girlfriend Ann Winblad's approval to marry his wife.

Gates and Winblad dated in the '80s and broke up in 1987, the same year of Melinda's joined Microsoft as a product manager. Despite breaking up with Ann, Gates continued to remain friends with her. The two often referred to each other in interviews and collaborated on business projects. 


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Why did Bill and Ann break up?

In 1984, Gates met Winblad at a Ben Rosen-Esther Dyson computer conference and they went on to date for three years. Gates and Winblad liked to go on "virtual dates" to keep their long-distance relationship going, even before people were forced to remote dating. They would watch the same movie at the same time and discuss it on the phone.

Ann Winblad (Getty Images)

However, that was not all. Gates and Winblad also went on a number of trips together, including to Brazil and central Africa. However, the relationship did not last long and part of the reason for the split was that Winblad, who is five years older to Gates, wanted to get married and he was still not ready. The former couple not only stayed in touch personally even after they split, but also in 1999, Bill and Ann teamed up as Hummer Winblad Venture Partners. 

Winblad's approval of Melinda and the bizarre agreement

When it was time for Bill Gates to propose to Melinda, he reportedly first sought Winblad's approval of this then-future bride. "When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval," Gates recalled to Time magazine in a 1997 article. As for Winblad, she told the outlet that she thought Melinda would "be a good match for him because she had intellectual stamina."

While recent court papers indicated that Bill and Melinda Gates did not have any existing prenup, some reports say that the estranged couple did in fact once have a prenup but it had more to do with Winblad than money. Apparently, when Gates and Melinda signed their prenup agreement, there was reportedly a clause in it that stated Gates was allowed to spend at least one weekend a year with his ex-girlfriend. After marriage, Gates continued his annual spring getaway with his former flame at her beach house on the Outer Banks of North Carolina, according to Time.

Microsoft founder and chairman Bill Gates shares the stage with his ex Melinda (Getty Images)

"Even now, Gates has an arrangement with his wife that he and Winblad can keep one vacation tradition alive," Walter Isaacson reported in the story. "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 at the time, "We can play putt-putt while discussing biotechnology" and 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." It is unclear if these trips are still carried out. 

Gates once had both Ann and Melinda's pictures in his office

Bill Gates once had a picture of Ann Winblad on a trip to Germany as well as a snap of his wife with nine friends on a 1995 vacation to Indonesia hanging in his office 24 years ago.

Melinda previously opened up that being with Gates was often “incredibly hard” in 2019, when they marked 25 years of marriage. “When he was having trouble making the decision about getting married, he was incredibly clear that it was not about me," she said. "It was about ‘Can I get the balance right between work and family life?”’

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