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Inside Bill Gates' Relationship With His Ex-Girlfriend: Billionaire Took Getaway Trips With Ann Winblad After Marrying Melinda

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Source: MEGA; CNBC/YouTube

May. 4 2021, Published 5:46 p.m. ET

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Before Bill and Melinda Gates announced the end of their 27-year marriage, the tech billionaire offered a glimpse into the former couple's longtime relationship — and it included him taking long, secluded getaway trips to a cozy beach cottage in North Carolina with his old girlfriend!

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Bill reportedly made the less-than conventional arrangement with his soon-to-be ex-wife as part of the deal when the two wed in 1994. "We can play putt-putt while discussing biotechnology," Gates said of his private retreats with ex Ann Winblad.

And it seems Bill's ex had a prominent role in his life, as he even sought her approval before proposing to Melinda. "When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval," he told Time magazine in a 1997 profile, adding that she gave Melinda the thumbs up.

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"I said she’d be a good match for him because she had intellectual stamina," Ann recalled.

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The 65-year-old — who announced he and Melinda were divorcing in a joint statement to Twitter on Monday, May 3 — said he and Ann, who met at a computer conference, started taking their annual trips to her Outer Banks home when they began dating in 1984. 

Despite calling it quits in 1987 — because Ann was reportedly ready to settle down as she was five years his senior — the close pair continued taking their yearly excursions.

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During their getaways, the two would ride dune buggies, hang-glide, take strolls on the beach and "share [their] thoughts about the world and [themselves]," she told the magazine. 

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"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," Ann, a software expert and venture capitalist from Seattle, Wash., added.

The tech experts began their relationship with virtual dates when they were in different cities. During their romance, they would reportedly go to the same movie at the same time and discuss the film over the phone.

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"Bill wasn’t such a big deal when I started dating him," Ann recalled while speaking to the San Francisco Chronicle in 2005, before joking: "And there was a period of time when my net worth was higher than his, and I had to pay for everything. It was a very short period of time, but it was memorable."

She also recalled a conversation she had with the ambitious Microsoft co-founder when he said he could see himself making "$500 million in revenue,” which was at least five times more than what any software company was doing at that time, the Silicon Valley Business Journal reported in 2013.

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"I remember making him take a stick or a rock and drawing the numbers out on the sand for me. He then said, ‘What troubles me is I can’t see how I am going to get past $500 million,'" she said of their chat, remembering how the duo would draw a "lot of inspiration from each other back then."

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During a 1996 interview with Wired, Bill gushed over Ann, calling her "incredibly smart," explaining that his former girlfriend “brings a sense of enjoyment and humor to even the most serious situations."

While Ann has remained in the picture years after the two called it quits, the fait of Bill and Melinda's relationship remains uncertain. 

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In the former couple's separation announcement, the parents to Jennifer, 25, Rory, 21, and Phoebe, 18, said they "raised three incredible children and build a foundation that works all over the world to enable all people to lead healthy, productive lives," referring to their nonprofit organization, the Bill & Melinda Gates Foundation.

However, Bill and Melinda decided to end their marriage because, according to their statement, "We no longer believe we can grow together as a couple in this next phase of our lives."

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