Bill Gates And Ann Winblad's Relationship Timeline

In early May of this year, news broke that Bill and Melinda Gates were separating, and people across the globe were shocked to learn of the dissolution of one of the most iconic billionaire couples in the world. Before Melinda entered the software developer's life in 1987, there was another woman standing by his side (via BBC). That woman was his former long-term girlfriend, Ann Winblad.

In true Gates fashion, the famed CEO met Winblad at a computer conference in 1984, according to the New York Post. In the early days of their relationship, the pair bonded by watching the same movies at the same time in separate locations, then discussing what they'd watched over the phone. Eventually, the pair began spending more time together in real life, off the phone, and they continued to date for several years. Winblad even became an early investor in Microsoft in the '80s. Their five year age gap reportedly contributed to their eventual split in 1987, as the slightly older Ann was looking for more of a long term commitment. Although the romantic partnership ended, the duo stayed close.

In a 1997 profile on Bill Gates for Time, journalist Walter Isaacson described Gates and Ann Winblad as kindred spirits, citing the couple's love of discussing the sciences and other various heavy topics while doing seemingly regular things such as playing putt-putt or enjoying vacations together. Gates maintained a deep level of respect for his past love following their split, even going so far as to request Winblad's approval before proposing to his former wife, Melinda, according to Newsweek. Luckily for the Gates, Winblad approved and the couple enjoyed a 27 year union and several shared business ventures. Although Gates married another woman, he kept Winblad in his life with his wife's blessing.

Gates and Winblad had enjoyed many vacations during their time together, and, while they stopped for most part following their split, the pair struck an arrangement that allowed Gates to take a weekend trip to Winblad's vacation home in the Outer Banks of North Carolina. Melinda granted Gates permission to keep the tradition alive, knowing that her husband would not give up his close-knit friendship with his former flame (via Newsweek). Though it seems that the tradition no longer continues, the two have maintained an amicable relationship over the years.