In 2021, Bill and Melinda Gates signed a separation contract for dividing their assets. At the time the couple had a US$130 billion fortune, and on the Forbes list of World’s Billionaires for 2022 , Bill remained at No 4 with a net worth of US$129 billion. Melinda was one of only 33 women on the list of 236 newcomers; she now has a net worth of US$6.2 billion. The high-profile separation shone a spotlight on the other women in Bill’s life. So just who else has he been romantically linked to? Inside Rihanna and A$AP Rocky’s rags-to-riches family life 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. How rich is Lady Gaga really? Inside her gigantic net worth 2. An affair with his interpreter? Shelly Wang – Bill’s interpreter who worked for the Bill and Melinda Gates Foundation from 2015 – responded to rumours that emerged on social media following the announcement the Gates couple was to go their separate ways. Apparently some believe that she was responsible for the split. “I thought that the rumours would go away by themselves, but I did not expect the rumours to become more and more crazily spread,” Wang, then 36, wrote on Weibo in May 2021. “I would like to thank everyone for their concern and help in dispelling the rumours through private messages in the past 24 hours.” Shelly Wang's responded today to the rumours from Fox alleging that she had “more than strictly professional relationship” with Bill Gates. She calls the whole thing "crazy" and tells people not to "waste time on unfounded rumours". pic.twitter.com/7wQdNhP2tO — Kerry Allen 凯丽 (@kerrya11en) May 5, 2021 It followed an official statement from the couple explaining why they had broken up. “After a great deal of thought and a lot of work on our relationship, we have made the decision to end our marriage . Over the last 27 years, we have raised three incredible children and built a foundation that works all over the world to enable all people to lead healthy, productive lives,” the statement read. “We continue to share a belief in that mission and will continue our work together at the foundation, but we no longer believe we can grow together as a couple in this next phase of our lives. We ask for space and privacy for our family as we begin to navigate this new life.” The luxury lives of Kourtney Kardashian’s children 3. His Hollywood star tennis buddy Elisabeth Shue has starred in The Karate Kid and Back to the Future II and, in March, all eyes were on her as she enjoyed a tennis game with Bill. The Oscar-nominated actress, 58, joined him at the Indian Wells alongside a woman described as a mystery brunette. I’m a big tennis fan, so I was excited to recreate this photo with my friend Elisabeth Shue from #BattleoftheSexes : https://t.co/QPDxH6wnhg pic.twitter.com/78dkR6pF9J — Bill Gates (@BillGates) September 27, 2017 In 2017, Forbes described Shue as Bill’s “frequent tennis (watching) partner”. Shue has been married to writer, director and producer Philip Guggenheim ( ER and NYPD Blue ) since 1994. 4. Was there a mystery lover? Bill has stayed tight-lipped about his love life after Melinda but, in March 2022, she shared in a CBS interview that although they had once worked through an affair he had with a Microsoft employee 20 years ago, the trust was no longer there. “It wasn’t one moment or one specific thing that happened. There just came a point in time where there was enough there that I realised it just wasn’t healthy, and I couldn’t trust what we had,” Melinda added. Want more stories like this? Follow STYLE on Facebook , Instagram , YouTube and Twitter .