Inside the Yearly Vacations Bill Gates Went on With His Ex-Girlfriend While Married to Melinda Gates

When most people break up with their partners and claim that they still want to be friends, they don’t really mean it. Bill Gates and ex-girlfriend Ann Winblad actually did. They maintained a close relationship throughout Bill’s entire marriage to his wife, Melinda Gates. The two weren’t just casual friends, either, they vacationed together once a year and Bill valued her opinion so much that he went to her before making big life decisions.

Bill Gates age 64 sitting against a blue background while speaking at a conference
Bill Gates | Takaaki Iwabu/Bloomberg via Getty Images

Bill and Ann Winblad’s relationship

Bill and Winblad went on virtual dates even before the coronavirus (COVID-19) pandemic made them a thing. After Winblad and Bill met at a Ben Rosen-Esther Dyson computer conference in 1984, the two would go on “dates” by driving to a movie and watching it at the same time in different cities and talking on the phone, according to Time magazine.

Winblad became an early investor in Microsoft and the two connected over shared interests.

“They were kindred minds as well as spirits,” the Time profile reads. “On a vacation to Brazil, he took James Watson‘s 1,100-page textbook, Molecular Biology of the Gene, and they studied bioengineering together. On another vacation, to a Santa Barbara, California, ranch, she took tapes of Richard Feynman‘s lectures at Cornell, and they studied physics.”

The two broke up in 1987 because Winblad was ready for marriage and Bill wasn’t. However when Bill did finally find someone he wanted to marry, he asked for Winblad’s permission.

“When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval,” Bill told the outlet. Winblad gave her blessing as she thought that Melinda had the “intellectual stamina” to keep up with Bill.

Bill Gates’ vacations with his ex-girlfriend

Even though Bill married someone else, he made sure that Melinda was OK with him still spending time with Winblad.

“Even now, Gates has an arrangement with his wife that he and Winblad can keep one vacation tradition alive,” the Time profile claimed in 1997. “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.”

According to Bill, the activities they engaged in on these trips were innocent enough.

“We can play putt-putt while discussing biotechnology,” he told the outlet.

“We share our thoughts about the world and ourselves,” Winblad added. “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 Gates and wife Melinda Gates’ divorce

Bill and his wife Melinda announced earlier this week that they would be ending their 27-year marriage.


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“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,” they said in a statement. “We ask for space and privacy for our family as we begin to navigate this new life.”