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Are Anna Wintour And Bill Nighy Dating? Here's The Gossip

Is iconic fashion director Anna Wintour dating LoveActually actor Bill Nighy? It certainly looks that way! The couple have been papped cosying up together several times over the last few months, so they've definitely sent the gossip mill into overdrive.

Related: All The Things Anna Wintour Has Admitted To Disliking

While holidaying in Rome last month, the VogueAmerica editor and veteran actor, both 71, were spotted dining together at up-market restaurant Pierluigi. Just a friendly catch-up perhaps? Oh no. For one of their meet-ups, Bill - who seems to be quite the old romantic - arrived with an armful of classic red roses and presented them to Anna as he arrived.

So what is going on between these two? Is it a serious thing blossoming between them, or are they keeping it relaxed for now? Let's find out.

6 Anna Recently Went Through A Divorce

Only last year, Anna went through a difficult split from her husband Shelby Bryan. She and the Texan telecoms businessman had been married since 1997 (though there are rumours that the couple never actually tied the knot), and were often sensationalised in the media as an impressive power couple at the time. Anna also has two grown-up children, Charles, 36, and Bee, 33, from her first marriage to David Shaffer, a professor of Psychiatry.

The break-up was difficult; though it was only officially over in 2020, the couple had been estranged from each other for several years prior to this, and had been freely dating other people during this time.

5 Bill Has Also Been Through A Tough Divorce

Anna isn't the only one who has been through a tough separation after so many years together. Bill split from his wife of 28 years, fellow English actress Diana Quick, 74, back in 2008, and has been recovering from the tough split ever since. The couple shared one daughter, Mary, 37. Though its been several years since their divorce, Bill has been tentative about starting a new relationship, so its no surprise that he and Anna appear to be taking things slowly.

4 They've Probably Been Seeing Each Other Since 2015

You may be surprised to hear that this isn't exactly a new thing between the About Time actor and Vogue Editor-in-Chief. They're rumoured to have been seeing each other romantically since as far back as 2015, having been repeatedly seen together at big fashion shows, theatres and restaurants around London and New York City. Things were tricky at the time, however, as Anna was still officially married to husband Shelby. So they were inclined to keep things quiet for this reason. Bill was understandably coy when asked about their relationship, and generally refused to comment on it - out of respect for Anna, who is notoriously private.

When asked about he and Anna back in 2015, he replied: “Obviously I have nothing to say about that. There are a lot of rumors about me and probably about Anna Wintour.”

3 Anna Hasn't Made Things 'Official' Yet

The pair evidently aren't ready to go completely public about their relationship just yet. Anna has yet to bring Bill along to big red carpet events as a couple, At the Met Gala two weeks ago, which Anna has always attended as chairwoman of the Institute since 1995, Bill was noticeably absent. Anna chose to invite her daughter Bee instead. Maybe they just aren't ready to step out together at big events just yet.

Related: Fans Are Torn By Anna Wintour’s Decision To Invite TikTok Stars To The Met Gala For The First Time

2 They've Been Having Lots Of Romantic Dinner Dates

Bill and Anna have been spotted at several restaurants together, but it was their date in Rome last month which really got people starting to speculate. Anna, who wore an elegant green Prada dress, was greeted by Bill who arrived with an armful of red roses (classic!) and the two dined al-fresco at a high-class eatery. They were seen engaging in close conversation, with Anna beaming and occasionally looking deeply into Bill's eyes. As they left, Anna gave Bill a huge hug. Yes, it could be love, actually.

Related: Fans Spill The Tea On Anna Wintour As ‘New Yorker’ Employees Protest Outside Her House

1 So What Does The Future Hold For These Two?

Its not completely clear what the next steps are for the couple. Anna is famously aloof and keeps all her relationships at arm's length, generally. She's even a mystery to some of her closest friends who have known her for years, so it may take Bill a little while longer to really get close to her and take their romance to the next level. Both are also extraordinarily busy professionals, so finding time to meet up between their crazy schedules may also be tricky. They seem to be finding time for each other, however, and are enjoying spending time together in casual settings. Hey, what's the rush?

What is clear is that Bill is definitely an old romantic at heart and is really trying to woo Anna to the best of his abilities. And she seems pretty receptive to it!

Next: Anna Wintour Is Wearing Sweatpants And Confirms Fashion Can’t Go Back

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Reinaldo Massengill

Update: 2024-09-20