Are Bill Nighy and Anna Wintour Hollywood’s newest couple? The Love Actually star and the Vogue editor-in-chief sparked romance speculation after they were spotted out to dinner in August 2021. This isn’t the first time rumors have swirled about a potential relationship between the two.

Bill and Anna looked happier than ever as they photographed in Rome, Italy, where they dined at the luxurious restaurant Pierluigi on August 26. According to the Daily Mail, the British-American journalist was seen holding a beautiful bouquet of roses, which was gifted to her by Bill.

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During their dinner date, Anna dressed to the nines in a long-sleeved white frock with a floral design. Bill, on the other hand, looked like a total stud in a black blazer, slacks and a white dress shirt. The two engaged in a long conversation while enjoying their delicious meals.

Since at least 2015, fans have wondered if there was more to Anna and Bill’s friendship considering they’ve made countless appearances together at fashion shows, theaters and restaurants in both London and New York City. Despite the speculation, it’s important to remember the September Issue star was married to her second husband, Shelby Bryan.

However, Anna and the American telecommunications pioneer quietly ended their marriage after 16 years in October 2020. Page Six reported the split at the time, revealing their relationship actually started to go south around 2013. “It’s been quite a while since they’ve been seen together,” a source told the outlet.

It seems now could be a perfect time for Anna and Bill to pursue their romantic chemistry, as the Pirates of the Caribbean alum is also reported to be single. Bill was previously involved with his longtime partner, Diana Quick, but they ended their relationship in 2008. The exes were together for 27 years and share their daughter, Mary Nighy.


Bill and Anna have yet to sound off on their potential love affair, but in 2015, the About Time actor made a brief comment about their connection. Speaking with Daily Mail, Bill said he wouldn’t reveal whether or not there was anything going on.

“Well, I have obviously nothing to say about that,” he stated. “There are a lot of rumors about me and probably about Anna Wintour.”

In addition to her marriage with Shelby, Anna was previously wed to her first spouse, Dr. David Shaffer, from 1984 to 1999. During their relationship, the ex-couple became the parents of their two kids, Charlie Shaffer and Bee Shaffer.