Bill Gates Dating History Revealed

Bill Gates isn’t a lady’s man. He’s a tech guy through and through with a thirty-year marriage behind him and a couple of partners before that. This guy’s dating history isn’t a long list of beauties attracted to him because of his massive fortune. It’s a short one of women he had relationships with. Of course, the list will grow now he’s split up with Melinda, but we do not expect to report on him dating a bevvy of beauties over the coming months. Before Bill met Melinda in 1987, he had two significant romances which left an impression on his life. Let’s find out what we can about Ann Winblad and Jill Bennett before we wonder where his love life will lead to next.

    By Frederic Legrand - COMEO on Shuttershock

Jill Bennett

Jill was his first serious girlfriend. They met at a party in Seattle in 1983, where they bonded over a shared love of tennis and computers. They also shared some mutual friends and were surprisingly close in age, born just one day apart. They were also born in the same hospital, so no wonder each of them thought the other was made for them. “We even look a little alike,” the then 27-year old told The Seattle Times. However, after a few years of dating, Bennett grew tired of his workaholic lifestyle. “He would often show up at her house dead on arrival,” James Wallace, the author of Overdrive: Bill Gates and the Race to Control Cyberspace, told The Post.

No distractions

The man’s drive for success was obsessive. That’s the sort of mindset that makes someone successful, but it also pushes people away. Once they were apart, Bennett would tell stories that showed just how far Gates would go to pursue success. She described him removing his car radio so he wouldn’t be distracted while brainstorming on long journeys. The couple remain friends. They even started the Mary Gates Lectureship Series in 2003 to honour Bill’s mum. Sadly, a year later, Bennett passed away after a courageous battle with breast cancer. Gates called her “…a remarkable human being — gifted, dedicated, and full of life.” He said that “She fought her cancer as bravely as anyone I’ve ever known. She never gave in — she actually found strength in bringing attention to the issue and inspiring people to work toward a cure.”

Ann Winblad

Gates began dating Ann Winblad in 1984 after meeting at a computer conference. As with Bennett, she remained part of his life after he married Melinda. She seemed to be more on his wavelength than Bennett. She was OK with their first dates being “virtual”. Back in the 1980s, that meant watching the same movies and then discussing them later when they were too far apart to see each other. They dated for three years, calling it quits in 1987 when Winblad was ready to settle, and Gates was not. They continue to be in touch with one another. “We share our thoughts about the world and ourselves,” she told Time. “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 centre of an amazing universe.” About six years ago, Winblad married Alex Kline, a private investigator with two children from a previous marriage.


If you believe the rumours, another woman played an important part in his life. The Microsoft mogul’s affair with an attractive young sales manager at Microsoft's German office is a rumour that won't go away. It was twenty years ago, so there’s little chance it’s the reason he and his wife have split up, but this unnamed lady had an impact on his life. Some say this short relationship led to the Microsoft founder stepping down from his position as CEO in 2000. The fact that someone in Melinda's inner circle hired a private investigator to look into this affair suggests it was an important relationship in his life.

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