Is Anna Wintour Dating Bill Nighy? It’s a Long Story

Anna Wintour and Bill Nighy at the Met Gala


The Vogue editor and actor are sparking romance rumors.

Anna Wintour’s illustrious career as Vogue’s editor-in-chief for the past 35 years has turned her into a pop culture icon, with her larger-than-life persona inspiring the 2003 book-turned-Hollywood movie, The Devil Wears Prada. Even with all of this attention, she has managed to keep her love life largely under wraps, so it’s probably no surprise that her date to the 2023 Met Gala stirred some excitement and speculation. 

On Monday, Wintour arrived at the annual fundraising event strolling arm-in-arm with actor Bill Nighy, who starred in the beloved 2003 rom-com, Love Actually. But before you eagerly jump to any conclusions, neither party has actually confirmed that they’re officially an item. 

A rep for Nighy even issued a statement shortly after their red carpet debut calling on everyone to simmer down: “Bill and Anna have simply been great friends for two decades,” they told The Independent in a post-gala statement. “They are not in a relationship.”

Nevertheless, this hasn’t stopped romance rumors from percolating. For the record, there have been whispers that the pair has been dating for many years, though that’s never been confirmed. Amid all of this juicy chatter, here’s what we know about the pair and some of Wintour’s past relationships. 

Is Anna Wintour dating Bill Nighy?

The idea of the fashion icon and rom-com star together doesn’t seem too far-fetched — the duo has been sparking dating rumors for years now (since 2010 to be exact). In 2018, the pair were spotted watching a play in London. Nighy quickly brushed off any gossip by saying, “There are a lot of rumors about me and probably about Anna.”

But the pair has continued to fuel dating rumors: In 2021, the pair was seen in Italy eating dinner together. At the time, the Daily Mail published photos of Nighy buying roses for Wintour before their meal. (If that isn’t a romantic gesture, we don’t know what is.) The pair made headlines the following year when Wintour arrived at the screening of Nighy’s period piece drama, Living. Once again, the tabloids seized on this, with The Telegraph reporting that the long-time friends were secretly involved in a romantic relationship. But, with both refusing to say a word, the nature of the pair’s relationship remains an enigma. 

Who was Anna Wintour married to?

The fashion mogul has always been a notoriously private person, but what we do know is that she has been married twice. In 1984, the style icon married her first husband, David Shaffer, a prominent child psychiatrist in New York. Before divorcing 15 years later, they had two kids together, Charles “Charlie” and daughter Katherine “Bee.” While Charlie followed in his father’s footsteps and became a psychiatrist, Bee went into television and worked as a producer on Late Night with Seth Meyers. Both her kids also have children of their own, making Wintour a proud grandmother of three.

Anna Wintour’s past boyfriends

In a decidedly more salacious vein, she’s also rumored to have had a week-long affair with Bob Marley in the 1970s, but denied that spicy tidbit when asked about it by James Corden during a 2017 interview on The Late Late Show:

After her divorce from Shaffer in 1999, Wintour started dating venture capitalist Shelby Bryan and the pair married in 2004. Though Shelby quickly became a fixture by her side at various fashion shows and public events, the pair reportedly split sometime before 2020 after growing apart for some time. “It’s been quite a while since they’ve been seen together,” a source told Page Six. 

As for Nighy, the actor has never been married, though he was previously in a long-term relationship with British actress Diana Quick from 1982 to 2008. (The former couple has a daughter, Mary Nighy, who’s also an actress and filmmaker). 

Now that the two appear to be free agents, it’s no wonder why Wintour and Nighy are having a hard time escaping dating rumors, but only time will tell whether the pair are lovebirds or really just friends.