There was another woman in Bill Gates’ life who he would vacation with annually without wife Melinda. We’ve got five things to know about venture capitalist Ann Winblad. Despite marrying wife Melinda Gates in 1994, Microsoft founder Bill Gates still continued to take annual weekend springtime getaways to his ex-girlfriend Ann Winblad‘s home in North Carolina’s Outer Banks. And Bill’s 56-year-old wife was aware of the arrangement. The pair would go for walks on the beach, ride dune buggies and go hang gliding. Bill, 65, dated Ann, now 70, in the 1980’s, all the way up until their 1987 split, which was the year he met Melinda. Bill was so close to Ann that he even asked for her approval when he was considering marrying his future wife. The pair has now split after 27 years of marriage, with Melinda filing for divorce. We’ve got five things to know about his ex, venture capitalist Ann Winblad.