So is it FINALLY Love, Actually? After that arm-in-arm Met Gala moment, ALISON BOSHOFF now reveals what’s really going on between Anna ‘Nuclear’ Wintour and Bill Nighy… from romantic vacations to front row flirting

  • Anna and Bill, both 73, seemingly confirmed long-running rumors of a romance between them when they made a joint appearance at Monday’s Met Gala 
  • But even as images of them together were being beamed around the world, Bill’s office in London was issuing a brief but clear denial that they are a couple
  • So if it is not Love, Actually, then how did this closeness arise – and will it eventually lead to a full-blown romance?

There can be no louder declaration of a relationship status than a walk up the red carpet – particularly if you are Anna Wintour and the red carpet in question is at the Met Gala, the biggest night in the fashion calendar and one that you just so happen to command. 

Nor could there be more clear a sign of love in the air than the almost girlish delight plastered across the infamously frosty 73-year-old’s face as she walked up the iconic Met steps arm-in-arm with British actor Bill Nighy, also 73.

Indeed, Nuclear Wintour – the less-than-flattering nickname bestowed upon Anna as a result of her demanding personality – appeared to have melted entirely as she leaned into her escort with a beaming smile, which he readily returned with a raffish twinkle.

The two of them have known each other ‘for decades’ and have been flirtatious friends since at least 2009, following the end of Nighy’s marriage to actress Diana Quick in 2008.

Anna Wintour and Bill Nighy, both 73, appeared to confirm rumors of a long-standing romance to the world when they made a joint appearance at Monday night’s Met Gala 

But even as images of them together were being beamed around the world, Bill’s office in London was issuing a brief but clear denial that they are a couple

And while rumors of their romance only began to swirl back in 2020, to outsiders, it definitely appears there has been a semi-public wooing going on for many years, even though for much of that time Anna was in a relationship with owlish Texan billionaire Shelby Bryan.

That Dame Anna and Bill have made their first official red carpet appearance as a pair at such a high-profile event is surely proof that what Anna wants, Anna gets. 

Or is it? For even as images of them together were being beamed around the world, Bill’s office in London was issuing a brief but clear denial that they are a couple. 

‘They are just friends. As simple as that,’ said his spokesman.

A pal added: ‘Seriously they are absolutely not dating. Never have. Just friends.’

So if it is not Love, Actually, then how did this closeness arise – and will it eventually lead to a full-blown romance?

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

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

Rumors of a relationship between the Vogue editor and the British actor (pictured together in 2020) have been swirling for years thanks to their regularly public appearances together

The pair’s so-called platonic relationship dates back to the early 2000s when they began getting to know each other through the British theatrical scene (seen together in 2010)

At some point in those early years of theatrical run-ins, Anna and Bill formed a close friendship and began to see each other socially whenever she was in London. 

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

In 2011 the friendship had grown close enough for Anna to quietly give Bill’s daughter a job; actress-turned-director Mary Nighy 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 others ears.

Anna, who has thrown her weight – and that of her publication – behind several celebrity pals over the years, including James Corden and Roger Federer, has also thrown several parties for Bill at her New York City townhouse. 

One such event in 2014 featured a screening of his film Turks and Caicos, and another held last year was thrown in honor of his movie 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 had a very coy response.

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

It was a staggering thing to say, and unsurprisingly set off a wave of gossip on both sides of the Atlantic.

Particularly because Anna was, at the time, in a relationship with her live-in boyfriend Shelby Bryan, an investor with whom she spent 20 years.

In fact a few weeks before Bill’s interview was published, Shelby had walked up the red carpet at the Met Gala five paces behind Anna (his customary position). The couple left the after party at the same time, although once again the financier trailed his partner at a respectful distance.

Anna and Bill even jetted off on a vacation to Rome together back in 2021

Over the years, Anna has hosted several parties in Bill’s honor, including a 2022 screening of his movie Living (pictured) 

Intriguingly Bill, who was living in New York for a few months while performing on Broadway, was also at the Met Ball, it is said at Anna’s personal invitation – although those within the actor’s inner circle were quick to deny that there was anything romantic between the pair. 

One friend of his said at the time that it was ‘100 per cent’ a platonic friendship between him and the editrix and nothing more.

‘They are good friends but there is no other relationship whatsoever,’ I was told.

Rather surprisingly, the offices of Vogue were more relaxed.

When asked about Bill and Anna’s relationship – and the actor’s appearance on the Met Gala red carpet that year – Lily Galef, Conde Nast’s Communications and Marketing assistant, said: ‘We will be unable to participate in this article. Please feel free to reach out with any future inquiries.’

Soon afterwards, Anna made her usual June trip to watch the tennis at Wimbledon. Her boyfriend Shelby was not by her side.

Then, in 2019, just months after her final public appearance with millionaire beau Shelby Bryan, Anna and Bill were seen twice dining at the Wolseley restaurant, just a stone’s throw from the actor’s fabulous Mayfair apartment.

The following year, Anna let it be known that she and Shelby were history – and less than 12 months later, she was seen enjoying a vacation with Bill in Rome. 

While official spokespeople might continue to insist that the relationship between the longtime ‘friends’ remains entirely platonic, there is no doubting that Anna and Bill’s joint appearance at the Met Gala on Monday night will have been carefully planned.  

Dame Anna is famously in control of everything – leaving lunches after 45 minutes, spending 20 minutes at parties, eating the same lunch, rising at the same time, and wearing the same couture Chanel day in and day out.

Long-time Vogue creative director Grace Coddington once remarked that she is ‘intentionally’ intimidating, and enjoys being feared. Apparently there is an unwritten rule which dictates that junior co-workers should never address her in conversation or ride the elevator with her. 

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

The Vogue editrix had a famously messy split from her first husband David Shaffer (seen together in 1991) – with whom she shares two children – back in 1999

Two years before announcing her divorce after 15 years of marriage, Anna had met investor Shelby Bryan, with whom she went on to enjoy a 20-year relationship 

Anna’s romance with Shelby (seen together at the Met Gala in 2005) came to an end in 2019 – and less than 12 months later she was pictured on vacation in Italy with Bill 

She declined, however, to address her personal life in any way.

Without a doubt she will be happy that she has managed to avoid a rerun of the messy, public 1999 split from husband David Shaffer, the father of her children Bee and Charles.

Two years before announcing their divorce after 15 years of marriage, Anna had met Shelby, a country club WASP with deep pockets at a political fundraiser in 1997. 

A year or so later, the affair was discovered and the matter became messily public – with reports of trysts in France and gifts of enormous emeralds.

Both Anna and Shelby returned to their spouses, with the latter reportedly agreeing to couples counselling with his wife Kathryn.

However within a few months of the scandal breaking, Anna and Shelby evidently decided they could not go back, and ended up with each other.

That Bill might have then charmed her out of Shelby’s arms is beyond a doubt possible.

A friend of mine, who got to know him on a film shoot, says he is ‘simply lovely, the most charming man – everyone who works with him falls in love with him.’

Actress Emily Blunt – who starred alongside Bill in the 2010 movie Wild Target – gushed: ‘He is my dear friend, I love the guy, he is an absolute hoot. 

‘He is a true gentleman of this business. What did he teach me? Some filthy language actually. And how to speed text. He’s very speedy.’

Bill’s only significant previous romance was with the iconic actress Diana Quick (seen together in 2012). They were been together from 1985 to 2008

Bill and Diana remain on very friendly terms – and even joined Anna on the front row of the Nicole Farhi fashion show in London back in 2012

Bill’s only significant previous romance was with the iconic actress Diana Quick. They were been together from 1985 to 2008.

Plagued by anxiety and chronic stage fright, he had a drinking problem when he and Diana met, but he eventually gave up drinking and drugs in 1992. He barely speaks about that period now, other than to say that there are no anecdotes to be shared because there was nothing fun about it.

‘I don’t think it’s big and I don’t think it’s clever and I don’t think it’s funny. For me it wasn’t funny at all and it is great when it finally stops,’ he said.

He told another interviewer: ‘The central fact of my life is that I have an unhealthy relationship with mood-altering chemicals, liquids and otherwise.

‘I never had a button other people seem to possess which tells you when to stop. It’s only when you’ve alienated everyone around you that you seek help.’

The son of a garage owner in Caterham, Surrey, Bill often says that he fell into acting almost by accident, at the suggestion of a girlfriend.

His first experiences were at the Everyman Theatre in Liverpool, where the resident writers were Willy Russell and Alan Bleasdale. He then went onto the National, and to professional alliances with David Hare, Tom Stoppard and Harold Pinter.

His relationship with Diana, famous for her role in the TV adaptation of Brideshead Revisited, ended in 2008 but they remain on good terms. Their split was variously blamed on him being a workaholic, and on her going to India to find her family roots for a book.

He lives a blissful bachelor life in Central London.

He likes to go out for coffee, and to bookshops, and is obsessed by football, particularly the fortunes of Crystal Palace.

It would be fair to say that he has an intense outlook on life, and on acting. He said: ‘I do love what I do some of the time. But, some of the time, it’s made me so unhappy I can’t tell you, [for] long periods of my life.’ Perhaps his equally intense companion – who isn’t quite a girlfriend – will guide him towards happier paths.

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