Anna Wintour and Bill Nighy Are Friends. People Really Want Them to Date.

Alaina Demopoulos
·3 min read
Photo Illustration by The Daily Beast / Photo Getty
Photo Illustration by The Daily Beast / Photo Getty

Anna Wintour, the inimitable editor-in-chief of Vogue and ultimate fashion maven, might not be a bastion of relatability for the average person. But she has one thing in common with the rest of us: If recent reports are true, she’s a big Bill Nighy fan.

According to the New York Post, Wintour has split with her partner of over 20 years, the “telecom millionaire” Shelby Bryan (this breakup allegedly occurred some time ago). He’s back in Texas and she remains in New York. The last time they were photographed together was at the 2018 U.S. Open, where they looked bored and rich together while watching tennis.

During their time together, Bryan reportedly “mellowed” Wintour and was the reason she “smiles now and has been seen to laugh.” Lovely stuff. But Bryan is not Bill Nighy, the acclaimed British character actor from Love, Actually and countless other beloved film roles.

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Bill Nighy is a longtime friend of Wintour; the two have been seen dining or attending fashion shows together for over a decade. A source opined to the Post that he is “kind of a Shelby look-alike.” In February, they were spotted “enjoying a cozy dinner together” in New York, according to Page Six.

Get this! Wintour took off her glasses during the date. This is potentially a huge deal, according to the tabloid. Wintour’s penchant for hiding her expression under thick black sunglasses is well-known. According to gossip logic, for her to take them off means she was having a really nice night.

“Anna was beaming the whole time,” the tipster told Page Six. “She looked happy and in very good company. She was beautifully made-up and she was smiling so much — she had her sunglasses off the entire time! They were sitting together in a corner enjoying a frothy coffee.”

Don’t you want to sit in a corner and enjoy a frothy coffee with Bill Nighy? Wouldn’t that be such a charming way to spend your evening?

Wintour, in her typical style, has yet to comment on the relationship. Nighy told the Daily Mail in 2015, “I have nothing to say about that. There are a lot of rumors about me and probably about Anna Wintour.”

Indeed there are. “Now That Anna Wintour is Single, Maybe She and Bill Nighy Can Be Together Forever,” a Jezebel headline from this week suggested.

The Daily Mail made its Friday lead story some drivel about how the U.K.’s “staying in rule does not stop the virus,” which is extremely whatever compared to the next block of text.

“Has ‘Nuclear Wintour’ found love, actually?” the headline screamed. It was placed underneath a photo of Wintour and Nighy posing together, her famous bob pressed up against his thick black glasses. Now this is the news we need to talk about.

“Tongues have been wagging about Wintour’s friendship with actor Bill Nighy,” the article read. The main evidence for a supposed affair: a photo of the two front-row at a fashion show, Nighy gazing admiringly at Wintour as she turned around to speak to someone else. The pair appeared to be snuggling up, or maybe it was just the fact that fashion shows are always crowded and leave even complete strangers basically sitting in each other’s laps.

Given Wintour’s reclusive reputation, it might take a while—if ever—to get an answer about what may or may not be happening with these two. Just know that if they ever get together, nearly everyone would be very happy and I for one promise to not overuse the “Love, actually” joke.

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