Cavill was first linked to the championship horse jumper in 2009 and he popped the question two years later. “I couldn’t believe it when he asked me to marry him,” Whitaker told the Belfast Telegraph in May 2011. “I thought we were there to celebrate his birthday. It was such a surprise and I am so happy.” However, the pair quietly called it quits in August 2012. “There was no fallout. They just both agreed it wasn’t working,” a source told Us at the time. “They broke up three months ago.”
In the fall of 2012, Cavill began dating The Mandalorian alum Gina Carano. “Gina is a complete firecracker. And she’s finally found someone who can handle her,” a source close to the actress told Us in June 2013. “She says they have a good thing going!” Though the duo split not long afterward, they rekindled their romance in October 2013 before ultimately breaking up for good in December 2014.
The Man of Steel star dated Cuoco for just 10 days in the summer of 2013. “Things fizzled as quickly as they heated up,” a source told Us in June of that year, just one day after the twosome were photographed in Los Angeles. “They are still friends.” “I had no one following me until I met Superman,” the Flight Attendant star told Cosmopolitan in April 2014 about their brief romance. “I’ve been in this business for 20 years, and my whole life, I could go anywhere, do anything. There had not been one paparazzi photo of me until like several months ago. The recognition was crazy.”
In February 2016, Cavill, then 33, attended the Vanity Fair Oscars party with his then-19-year-old girlfriend, King. The Man From U.N.C.L.E. star faced some backlash for their 13-year age difference, but he defended the relationship in an Elle interview that same month. “People say, ‘Age is just a number.’ A lot of times it’s not just a number. It’s actually a real and true sign of someone’s maturity. But in this case, she’s fantastic,” Cavill said, adding, “It’s a natural reaction. But when I was 19, I was going out with a 32-year-old.”
The Night Hunter star met stuntwoman Cork while on the set of Mission: Impossible — Fallout in 2017. The former couple dated for around a year before quietly calling it quits.
In April 2021, Cavill made his romance with Viscuso Instagram official, writing, “This is me looking quietly confident shortly before my beautiful and brilliant love Natalie, destroys me at chess.” The Legendary Entertainment television and digital studios vice president shared the same photo on her own page, with a slightly different caption. “Just teaching my dear Henry how to play some chess…or…maybe he let me win? 🤷🏼♀️” she wrote at the time. The couple made their red carpet debut in October 2022 at the Enola Holmes 2 premiere.
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