Bill Gates continued spending time with ex-girlfriend during marriage to Melinda

On Monday, Bill Gates announced via Twitter that he and his wife of 27 years were filing for divorce. Before marrying Melinda, Gates had dated Ann Winblad, a quirky venture capitalist five years his senior. According to a 1997 interview with Time Magazine, "They met in 1984 at a Ben Rosen-Esther Dyson computer conference and started going on 'virtual dates' by driving to the same movie at the same time in different cities and discussing it on their cell phones."

Winblad appeared to have quite the effect on Gates; it was reported that at one point, he even gave up eating meat because she told him to. The pair were described as "kindred minds as well as spirits", and more often than not spent their time learning together. According to Time Magazine, even on vacations, they'd bring along a biology textbook to read, or tapes of physics lectures to listen to.

They broke up in 1987 due to differing desires for the future, yet remained close; Gates even asked Winblad for approval before proposing to Melinda. Winblad thought the two would be a good match, citing her "intellectual stamina."

Even after getting married, Gates continued to see Winblad once a year, as per the agreement he had made with his wife. He and Winblad would meet, alone, at her beachfront cottage in North Carolina. "We'd share our thoughts about the world and ourselves", said Winlbad. "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." Gates put it more simply, stating that they "play putt-putt while discussing biotechnology."

The tradition of meeting up for a long weekend spanned nearly four decades, from the days of Gates and Winblad's time as a couple, through their marriages.