Who has Bill Gates dated? Before Melinda, the Microsoft billionaire was linked to Hollywood star Elisabeth Shue, an interpreter and his ‘one that got away’ ... Ann Winblad

- Melinda Gates, newcomer to Forbes’ billionaires list, cited a loss of trust as reason for divorce, while Bill’s interpreter Shelly Wang denied having an affair with him
- Bill remained friends with his ex, tech investor Ann Winblad, throughout his 27-year marriage; but was he really just tennis buddies with Hollywood’s Elisabeth Shue?

The high-profile separation shone a spotlight on the other women in Bill’s life. So just who else has he been romantically linked to?
1. The one that got away

When Bill and Melinda revealed they were to get divorced, attention turned to the billionaire’s ex-girlfriend, Ann L. Winblad. Winblad, an American businesswoman, dated the Microsoft founder in the 1980s and the pair maintained a close bond in the 1990s. They didn’t get married before their relationship ended in 1987 because, at the time, Bill wasn’t sure he was ready.
However, he asked for Winblad’s opinion before popping the question to Melinda in 1993, according to Time. Bill spent time with the tech investor throughout his relationship with Melinda. He and Winblad – who travelled a lot when they were still a couple – even took a spring trip to her beach house in North Carolina every year.

“We can play putt-putt while discussing biotechnology,” Gates told Time. Winblad, who is five years older, said in the magazine’s 1997 profile: “We share our thoughts about the world and ourselves. 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 centre of an amazing universe.”
Winblad got married in 2015 to a private investigator named Edward Alex Kline, according to media reports. He is the brother of actor Kevin Kline. It’s unclear whether Bill and Winblad still have their spring break arrangement nowadays.
2. An affair with his interpreter?
