For nearly three decades, Bill and Melinda Gates reigned as one of world’s most high-profile power couples — but the billionaire computer genius’ estranged wife wasn’t the first woman to fire up his hard drive.
Before Gates met Melinda in 1987, the Microsoft co-founder had at least two other major romances, both of which left a lasting impression on his life.
Here’s what is known about Gates’ two ex-girlfriends, Ann Winblad and Jill Bennett, as well as details of his courtship with his future wife.
Jill Bennett
Bennett, who has been described as his “first serious girlfriend,” met Gates at a party in 1983 in Seattle’s Madison Park neighborhood, where the pair bonded over tennis, computers and mutual friends.
Born a day apart at the same hospital, the then-27-year-olds marveled over how much they had in common, the Seattle Times reported.
“We even look a little alike,” Bennett told the newspaper.
But after dating for a couple of years, the computer sales rep eventually grew tired of Gates’ workaholic lifestyle.
“He would often show up at her house dead on arrival,” James Wallace, author of the 1997 biography “Overdrive: Bill Gates and the Race to Control Cyberspace,” told The Post.
She described how Gates even took the radio out of his car, so as not to distract him from brainstorming about his business.
“He was always multitasking. His attention wasn’t 100 percent on her. He was always thinking about all the other computer stuff,” said Wallace, who interviewed Bennett about Gates.
But the former couple stayed close as friends, with Bennett even creating the Mary Gates Lectureship Series in 2003 to honor Bill’s mother, who died of cancer, the Seattle Times reported.
Bennett was also diagnosed with breast cancer, working for years to find a cure before ultimately succumbing to the disease in 2004, the newspaper reported.
Bill paid tribute to his ex-girlfriend, calling her battle with the disease courageous.
“She was a remarkable human being — gifted, dedicated, and full of life,” he said. “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
Winblad was another ex-girlfriend who stayed for years in Bill’s life even after he walked down the aisle with Melinda.
The pair began dating in 1984, after meeting at a computer conference, Time reported in 1997.
What followed was a series of “virtual dates,” where they would watch the same movies at the same time and then discuss, the magazine reported.
But the couple called it quits by 1987, when Winblad, who is five years older than Gates, was reportedly more ready to settle down.
Still, they continued to take a yearly trip to Bill’s Outer Banks home.
“We share our thoughts about the world and ourselves,” Winblad, a software expert and venture capitalist from Seattle, Wash., told the magazine.
“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.”
The getaways didn’t stop when he married Melinda, who reportedly gave her husband her blessing to continue them.
“We can play putt-putt while discussing biotechnology,” the Microsoft mogul told the magazine of the trips.
Winblad has since married Alex Kline, 63, a private investigator with two adult kids from a previous marriage, a source told The Post. They wed about six years ago.
Melinda French Gates
When the Microsoft co-founder met his future wife at a trade show in New York in 1987, it wasn’t exactly love at first sight.
“When we first met, she had other boyfriends, and I had Microsoft,” Bill said in a 2019 Netflix docuseries “Inside Bill’s Brain: Decoding Bill Gates.”
She briefly worked for the company in its marketing department before she was appointed as general manager of information products in the early 1990s.
But somewhere along the line, they found they had a romantic connection.
“I think [Bill] wanted someone that had a lot of intellectual curiosity. They had a lot in common that they could talk about,” Wallace, Bill’s biographer, told The Post.
Bill reportedly even consulted his ex, Winblad, before proposing and made a pros and cons list about whether to commit.
“He made a list of the dos and don’ts for getting married. Here’s all the pluses for getting married and here’s all the negative,” Wallace said.
Bill and Melinda tied the knot on New Year’s Day in 1994 in Hawaii.
The two welcomed their first child, daughter Jennifer, in 1996, followed by their son, Rory, in 1999 and daughter Phoebe in 2002.
The pair announced their split on May 3, after 27 years of marriage, saying they “no longer believe we can grow together as a couple in this next phase of our lives.”
The divorce announcement was followed by Gates confirming that he had an affair during their marriage with an unnamed Microsoft employee, though he said the relationship was in 2000 and ended “amicably.”
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