“Anna Wintour and Bill Nighy’s ‘special’ friendship has long fuelled dating rumours (Picture: Angela Weiss/AFP via Getty Images) The Met Gala is the prime place for hot Hollywood gossip, especially as far as romance is concerned. From Kim Kardashian and Kanye West to Rihanna and A$AP Rocky, the annual fashion extravaganza has seen plenty of”, — write: metro.co.uk
Anna Wintour and Bill Nighy’s ‘special’ friendship has long fuelled dating rumours (Picture: Angela Weiss/AFP via Getty Images) The Met Gala is the prime place for hot Hollywood gossip, especially as far as romance is concerned.
From Kim Kardashian and Kanye West to Rihanna and A$AP Rocky, the annual fashion extravaganza has seen plenty of A-list couples grace the carpet in elaborate designer ensembles over the years.
But in recent times, Vogue editor-in-chief Anna Wintour herself has set tongues wagging with her own dating life.
The media executive and all-round powerhouse has been working on the Met since 1995, when she served as a co-chair. Four years later, she took the helm and has been curating starry guest lists and fine-tuning the dress code ever since.
For 2025, she’ll oversee the Superfine: Tailoring Black Style theme, with Pharrell Williams and Lewis Hamilton among co-chairs as the event returns to fundraise for the Metropolitan Museum’s Costume Institute.
Anna, 75, typically flies solo at the Gala – she’s Anna Wintour, no accessories needed. But everyone’s ears pricked up when she arrived at the 2023 Met with actor Bill Nighy on her arm…
The pair have been close friends for over 20 years (Picture: Stephen Lovekin/Shutterstock) Is Anna Wintour dating Bill Nighy? Dating rumours between Anna and Love Actually icon Bill, also 75, spread like wildfire two years ago when they rocked up to the Met Gala linking arms.
Making no secret of their affection for one another, they happily posed for photos, with Anna beaming in vibrant floral attire as Bill paid homage to the late Karl Lagerfeld in a dark suit.
Neither Anna nor Bill explicitly confirmed that they were an item, and no comment has been given since on whether they crossed the line from platonic to romantic.
However, after catching everyone’s attention at the Met, a spokesperson for the Golden Globe winner said: ‘Bill and Anna have simply been great friends for two decades. They are not in a relationship.’
They attended the 2023 Met Gala arm-in-arm (Picture: Erik Pendzich/Shutterstock) How long have Anna and Bill known each other? Anna and Bill have enjoyed a ‘special’ friendship for over two decades.
They first got to know each other in the early 2000s via the British theatrical scene, and they’ve attended many of the same events over the years.
Anna’s father founded the Evening Standard Theatre Awards, so she’s always had a keen interest in performing arts; hence, she attended the opening night of The Vertical Hour on Broadway in 2006 to support Bill in his starring role.
Whenever jet-setter Anna was in London, she and Bill would meet up socially, and their connection started strengthening in the late 2000s.
The pair were seen at theatre performances together, and, in 2009, they left a show before the second half to go for dinner instead.
Anna was also close with Bill when he was married to Diana Quick (right) (Picture: Samir Hussein/Getty Images) In 2011, Anna also gave Bill’s daughter, Mary Nighy, a job, as she was hired to shoot a short film inspired by that year’s Met Gala for Vogue.
Through the following years, Bill continued to show an interest in Anna’s world just as she did with his, as they sat together at various fashion shows in the capital.
Whenever they’ve been seen together at high-profile events, the two have greeted one another with sweet kisses on cheeks and whispers in one another’s ears.
Although it’s believed that behind closed doors, things can get pretty rowdy in their circle, as Anna has thrown many parties for Bill at her New York townhouse.
The only real time either has addressed the speculation that they are something more than friends is when Bill played coy in a 2015 interview about his love life.
Asked by the Wall Street Journal if he was dating someone, he replied: ‘Well, I have obviously nothing to say about that.’
Anna married David Shaffer in 1984, and they had two children (Picture: Ron Galella, Ltd./Ron Galella Collection via Getty Images) He then quipped that ‘there are a lot of rumours about me and probably about Anna Wintour.’
It’s safe to say people have been keeping a close eye on them since.
Who has Anna Wintour dated? Since her teens, Anna has been linked to men much older than her. She was briefly involved with writer Piers Paul Read when she was just 15. He was 24.
She also dated gossip columnist Nigel Dempster, and they were frequent faces on the London club scene.
Her second long-term romance was with entrepreneur Shelby Bryan (Picture: Dimitrios Kambouris/Getty Images for Novak Djokovic Foundation) In 1984, Anna married child psychiatrist David Shaffer. The following year, they welcomed a son, Charles.
They also had a daughter, Katherine, in 1987, before splitting and divorcing officially in 1999.
Anna’s second long-term partner was Shelby Bryan. In 1999, it’s believed they began an affair after meeting at a benefit ball for the New York Ballet.
Having both ended their marriages, they started living together in Greenwich Village, and the entrepreneur often accompanied Anna to glam events. They split in 2020.
Who has Bill Nighy dated? 
Bill’s split from actress Diana was shocking, as the world believed they were rock solid (Picture: Dave Hogan/Getty Images) In 1982, Bill began a relationship with English actress Diana Quick, having both played in David Hare’s A Map of the World.
They welcomed daughter Mary in 1984, and despite being viewed as a rock-solid couple following over two decades together, they split in 2008.
It’s believed Bill and Diana kept their breakup private for 18 months, with Diana’s own sister only finding out through the media.
Speaking to the Daily Mail previously, a friend of Bill’s mused over why their relationship turned sour.
‘It’s pretty well-known among his friends that Bill has had a bit of a funny turn,’ they began.
‘I suppose you could call it a delayed midlife crisis. After years of muddling through, he found huge success pretty late in life, and he hasn’t dealt with it especially well. He’s been working himself silly, and it’s not good for him.
‘He neglected Diana for years, and I think she finally got sick of it. There was some sort of ultimatum, and she left.’
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