The Love Actually star tied the knot in 2018, but his love life has been a topic of conversation since the 1980s. Grant made headlines in 1987 when he and Remando Al Viento costar Elizabeth Hurley began dating — and again in 1995 when he cheated on her.
The duo were one of the hottest couples in England before they called it quits in 2000 after 13 years together. Their relationship, however, wasn’t without its faults. In 1995, Grant was caught having an affair with sex worker Divine Brown, which he later attributed to his lack of confidence as an actor. (He and Hurley overcame the cheating scandal but ultimately called it quits in 2000.)
“I was about to launch my first Hollywood film – my timing was impeccable. My problem was – that was my first Hollywood film and I’d just been to see it,” the Rewrite actor explained during a March 2021 appearance on Marc Maron’s “WTF” podcast. “The film was about to come out a week or two after that, and I had a bad feeling about it. I went to see a screening. Everyone in it was brilliant, but I was so atrocious that I was not in a good frame of mind.”
Despite Grant’s indiscretion — and their split — the U.K. native “remains my best friend to this day, but … he really used to annoy me,” Hurley said during a March 2015 appearance on Watch What Happens Live With Andy Cohen. “I love him, but he’s very annoying.”
Grant echoed his ex’s sentiments during a 2018 interview on The Jess Cagle show. “We’re like brother and sister,” he confessed. “I think it’s partly because we went from zero to somewhere together, and we went through terrible years at the beginning when neither of us had any work, living in a tiny flat. It was quite bonding.”
While Grant’s relationship with Hurley has stayed intact over the years, his road to being a married man was a little more complex. The Notting Hill actor raised eyebrows in the mid-2000s when he welcomed three children back to back with two different women.
The two-time Emmy nominee became a first-time dad to daughter Tabitha in fall 2011 with his then ex-girlfriend Tinglan Hong. One year later, he and Eberstein welcomed their son, John. A few short months after that, Grant and Hong became parents to son Felix in February 2013.
Despite being in his 50s, the Gentlemen actor chose to embrace fatherhood and all it had to offer.
“It’s made me much nicer,” Grant exclusively told Us Weekly in February 2015 of becoming a parent. “One of my kids is very obsessed with saying goodbye — he’s only 2 — to everyone, including the man who delivers the groceries, whoever he might be. He has to have a hug and a kiss and I find that very charming.”
While the Paddington star was excited to be a dad, he was still unsure about saying “I do” to partner Eberstein, whom he went on to welcome two more children with between 2015 and 2018.
“If you ask me the question, ‘Do I think human beings are meant to be in 40-year-long monogamous, faithful relationships?’ No, no,” Grant told Howard Stern on his SiriusXM radio show in August 2016. “Whoever said they were? I think there’s something unromantic about marriage. You’re closing yourself off.”
Two years later, the Undoing alum wed Eberstein. He confessed during a June 2018 Today show appearance that marriage is “really nice. I can’t pretend it isn’t.” Grant added: “I should have done it before! But I’m just lucky, I’m lucky. I’ve got a great wife. I love her, yeah.”
Scroll down to relive all of Grant’s high-profile relationships: