A look at Bill Nighy and Anna Wintour’s relationship and their former romances

Bill Nighy and Anna Wintour confused fans when they seemed to confirm their “romance” on the Met Gala red carpet, only to insist they were just friends.

The last Met, held on the first Monday in May each year, was especially significant for Anna, 73, who attended on Bill’s arm and tongues after years of speculation that they’re an item.

However, a rep for Bill, 73, poured cold water on the rumors when they announced the next day: ‘Bill and Anna have just been good friends for two decades. They have no relationship.’

So if it’s not actually love, how did this closeness come about – and will it eventually lead to a full-fledged romance?

MailOnline takes a look at how their special friendship blossomed and the couple’s previous relationships.

When did Bill Nighy and Anna Wintour meet?

The pair’s so-called platonic relationship dates back to the early 2000s, when they started getting to know each other through the British theater scene.

Anna – whose father ‘Chilly Charlie’ Wintour founded the Evening Standard Theater Awards – and Bill have attended many of the same events over the years, and in 2006, when the actor starred in Broadway’s The Vertical Hour, the Vogue editors were there to offer her support while attending the opening night.

At some point in those early years of theatrical encounters, Anna and Bill formed a close friendship and began seeing each other socially whenever she was in London.

In 2009, they were seen leaving a theater performance together during intermission and going out to dinner together instead of staying for the second half of the play.

By 2011, the friendship had grown close enough for Anna to quietly get Bill’s daughter a job; Mary Nighy, actress and director, was commissioned by Vogue to shoot a short film, Jonnie and Ari, inspired by the punk theme of that year’s Met Ball.

In 2010, 2012 and 2013, the not-a-couple sat together at the Nicole Farhi fashion show in London.

On all occasions they greeted each other with a kiss and whispered in each other’s ears.

Anna, who has thrown her weight—and that of her publishing—behind several famous friends over the years, including James Corden and Roger Federer, has also hosted several parties for Bill at her New York City mansion.

One such event in 2014 was a screening of his film Turks and Caicos, and another event held last year was organized in honor of his film Living.

In 2015, during an interview with the Wall Street Journal, Bill was asked if it was true that he was dating someone – a question to which the actor responded very coyly.

‘Well, of course I have nothing to say about that,’ he said, before adding what appears to be a moment of blazing indiscretion: ‘there are a lot of rumors about me and probably about Anna Wintour.’

It was mind-boggling to say and unsurprisingly sparked a wave of gossip on both sides of the Atlantic.

Especially since Anna was dating her live-in boyfriend Shelby Bryan at the time, an investor she spent 20 years with.

In fact, a few weeks before Bill’s interview was published, Shelby had walked onto the Met Gala red carpet five steps behind Anna (his usual position). The couple left the afterparty at the same time, although the financier again followed his partner at a respectful distance.

Intriguingly, Bill, who lived in New York for a few months while performing on Broadway, also attended the Met Ball, reportedly at Anna’s personal invitation – though those within the actor’s circle were quick to deny there was anything romantic between the couple.

A friend of his at the time said it was “100 percent” a platonic friendship between him and the editrix and nothing more.

While official spokespersons may continue to insist that the relationship between the old “friends” remains completely platonic, there’s no doubt that Anna and Bill’s joint appearance at Monday night’s Met Gala will have been carefully planned.

Dame Anna has everything under control: leaving lunches after 45 minutes, spending 20 minutes at parties, eating the same lunch, getting up at the same time, and wearing the same Chanel couture day after day.

To pave the way for her red carpet debut with Bill, she granted a rare interview to The Times newspaper, selecting an interviewer who had previously profiled Bill for the paper.

Who has Bill Nighy dated?

Bill has not made a relationship public since he split from his long-term partner Diana Quick in 2008, with whom he shares a daughter, Mary.

The pair had been together for 27 years and their union was known as one of the most solid in show business.

That’s why fans were shocked when it emerged that they had called off their romance, with the pair initially keeping their split a secret for 18 months.

Relatives told The Daily Mail that not only did the couple hide the divorce from the public, Diana’s sister Julie was also in the dark until she read about it in a newspaper.

Speaking to the paper about what went wrong in the relationship, a friend of Bill’s said, “It’s pretty well known among his friends that Bill has had a bit of a funny twist.

You could call it a delayed midlife crisis. After years of muddling through, he found huge success quite late in life and hasn’t handled it particularly well. He’s made a fool of himself and that’s not good for him.

“He neglected Diana for years and I think she finally got fed up. There was some kind of ultimatum and she left.’

Plagued by anxiety and chronic stage fright, he had a drinking problem when he and Diana met, but eventually gave up drinking and drugs in 1992.

He hardly speaks about that period now, other than to say that there are no anecdotes to share because there was nothing fun about it.

“I don’t think it’s big and I don’t think it’s smart and I don’t think it’s funny. For me it wasn’t funny at all and it’s great when it finally stops,” he said.

Who has Anna Wintour dated?

Wintour’s first marriage was to David Shaffer in 1984, who was 10 years her senior. They had two children, Charles and Bee, but in 1999 the couple divorced and Anna began dating Shelby Bryan.

The chemistry between Anna and Shelby was evident from the moment they met in November 1997, when they sat next to each other at a New York City Ballet gala – both were married to other people.

At the time, Shelby was considered a Democratic Party rainmaker, having raised $1.5 million for candidates, including Al Gore, in fundraisers at his Upper East Side home. He also served on Clinton’s Foreign Intelligence Advisory Board.

He and Anna were certainly more than a match for each other.

The unabashedly ambitious Anna was then described as the “godmother” of the fashion mafia, while Shelby was described in a 1999 New York Magazine article as a “flashy extrovert with undisguised social ambitions.”

However, the relationship was said to have run into trouble in 2013 when it was revealed that he owed $1.2 million in back taxes to the IRS.

The pair were often photographed at social events and tennis matches in the years before, but have been spotted less often since then.

In 2020, the couple announced that they had split after 20 years together.