Bill Gates’ Friend Ann Winbald Played An Odd Role In His Marriage To Melinda French Gates

Bill and Melinda Gates had one of the most powerful, influential marriages of modern history. They put a close to that chapter when they announced their plans to get divorced after 27 years of marriage.

Despite having such a high-profile lifestyle, the details of their relationship weren't always clear. Sure, they presented a loving and united front, but most fans of the couple never felt like they knew their dynamic all that well despite the many lovely things they had to say about each other over the years.

As the two forge ahead on their own paths, many are wondering what could have brought them to the decision to split. We may never get an answer to that question, but there have been some moments throughout the years that brought insight and clarity into what their relationship was really like.

Bill and Melinda Gates' relationship was the result of total chance, in the way many iconic relationships often are. The two met when Bill sat down next to Melinda at a Microsoft event in 1987.

"When I moved to Seattle to take the job at Microsoft … I knew I would meet Bill because the company was small," Melinda recalled in a 2019 video celebrating Valentine's Day.

"But I certainly had no idea that I would fall in love with Bill or that we would get married."

At first, Melinda wasn't altogether interested. "When Bill first asked me out, he said, 'I was thinking maybe we could go out two weeks from tonight.' I told him he wasn’t spontaneous enough for me," she shared on his birthday in 2015.

"So he called me an hour later to suggest we get together that night. He asked: 'Is that spontaneous enough for you?'"

After about a year of dating, Bill felt himself at a crossroads. He knew he cared about Melinda a lot, but he struggled with whether he could handle marriage and an endeavor as big as Microsoft.

"I took the idea of marriage very seriously," Bill revealed in the three-part 2019 Netflix special, Inside Bill's Brain: Decoding Bill Gates.

"You know, we cared a lot for each other and there were only two possibilities: either we were going to break up or we were going to get married."

"When he was having trouble making the decision about getting married, he was incredibly clear that it was not about me, it was about 'Can I get the balance right between work and family life?'" Melinda told The Times.

Bill had so much trouble weighing the decision that he made a pros and cons list about getting married on a white board. Melinda happened to walk in and see him working on it.

At The 1987 PC Forum
Ann E. Yow-Dyson/Getty Images

Bill even asked his ex-girlfriend, Ann Winblad, what she thought of him marrying Melinda. He dated Ann from 1984 to 1987, so not only was she an ex, but the ex prior to him dating Melinda. In fact, Bill and Ann broke up because Ann, who is five years his senior, wanted to get married but Bill wasn't there yet. It makes him involving her in the situation all the more unusual.

"When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval," he told Time in 1997.

Software Millionaire Ann Winblad
Roger Ressmeyer/CORBIS/VCG via Getty Images

That wasn't the only role Ann played in their story. Bill also took annual vacations with her, with Melinda's blessing.

"Even now, Gates has an arrangement with his wife that he and Winblad can keep one vacation tradition alive," the profile of Bill revealed.

"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."

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Ann even spoke with Time about her relationship with Bill and their vacations together.

"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."

Life took a shift after Bill and Melinda married. As they started a family, Melinda stepped back from her role at Microsoft and focused on being a hands-on mom to their three kids. The fact that she did that surprised Bill, who always wanted to keep their partnership equal.

"He was surprised, he was definitely surprised," she recalled in a 2017 interview with CBS This Morning.

"But I said to him, 'You know, it just doesn't make sense. You can't be the CEO and go as hard as you're going and — somebody has to be at home, right? We didn't want our children raised by somebody else. I said, 'You know, if we want them to have the values we have, somebody has to be home.'"

Melinda returned to working when the kids got older, even stepping into a more public role.

"While I'd once thought the best thing I could do for my family was leave the workforce, as my kids and I both got a little older, I decided the most important thing I could do for them was go back," she wrote in Marie Claire.

"That decision is personal for each woman, but for me, it came down to this: If I wanted my daughters and son to truly believe that women can do anything, I needed to model that for them."

It's unclear how divided things will become as Bill and Melinda separate their lives. It's also unclear why they've decided to split, though the filings say the marriage is "irretrievably broken."

"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," the statement announcing their separation read.