Jack Whitehall blamed himself for ruining his first long-term celebrity romance, scuppering their chances of marriage.
Brit Awards 2025 host Jack Whitehall, 36, is currently engaged to his partner, model Roxy Horner, 33, and the couple share daughter Elsie together. They announced her arrival in September 2023 and in December last year, they revealed they had got engaged.
It’s thought comedian Jack popped the question in a festive setting surrounded by Christmas trees and fairy lights. Roxy shared pictures on social media of what appeared to be their hotel room full of balloons with two caps in black and white that read 'bride' and 'groom' on a table. She also flashed her large diamond sparkler of a ring in other snaps.
However Jack hasn’t always been so romantic and previously revealed that he totally messed up his first chance of tying the knot. He was in a serious relationship with Crazy Rich Asians actress Gemma Chan for six years until 2017 when they split. At the time it was thought they went their separate ways after struggling to spend time together because of their hectic work schedules. However Jack later admitted it was his fault they broke up and said they could have actually married.
In the fourth series of his Netflix series Travels With My Father, he confesses to his mother that he was to blame. "I f***ed up my chance of that. I did. I could have got married but I messed it up," he revealed. He also apologised for not being able to take a partner to his sister Molly’s upcoming nuptials and for what he might do on her big day.
"I’m sorry I’ll be attending the wedding alone and I’m sorry you have two children who have model relationships and one who is going to be there on his own maybe trying to sh*g a bridesmaid," he joked.
During one of his stand up shows he spoke about his split from Gemma and the real reasons behind it. "I’ve had a lot of changes in my life recently," he admitted. "I’m single now. I was in a relationship, it broke down, it was not gonna work, it was a long distance relationship, not geographically, just in terms of our expectations. She wanted kids now whereas I wanted to escape. I’m not good with kids."
Despite this he explained that it was an amicable split but said that didn’t help him when it came to material for his shows. "The one advantage at having tragedy in your life is you get material out of it," he said. "And she couldn’t even do that. No one has ever written an album about a wonderful break up where everyone behaved impeccably. I wanted her trampling my heart into the floor, she took my mum for tea to help my mum transition through the split. F*** you with your generosity."
In between his long-term relationships with Gemma and Roxy, Jack was known to be something of a lothario who enjoyed lots of rumoured dalliances with beautiful and talented women. One very unlikely affair was reported to be with US heiress Paris Hilton. Gossip started after she left a number of flirty reactions on his social media posts in 2019, including a heart eye and a fire emoji.
It’s believed they first met in London and he was invited to her 38th birthday party, with him liking her post about the event featuring her swirling around a pole in a glittery and daring body suit. "He was at her birthday party on March 16. She was overheard telling friends she thinks he is not only gorgeous but brilliant and hilarious," a source told HollywoodLife . "Paris and Jack met in London," they added.
Not long before the Paris ‘liaison’, Jack was apparently seen smooching in November 2018 with English actor Kate Beckinsale, who is 15 years his senior. The 51-year-old reportedly enjoyed the Decline and Fall's company at a Hollywood bar and was also spotted with him at a luxury hotel. "No one would expect someone like Jack to bag one of Hollywood’s hottest actresses. You couldn't get a more unlikely romance," an insider revealed to the Sun at the time, before describing the pair as "loved-up teenagers".
Jack first hosted the Brit Awards in 2018, in which an encounter with pop star Dua Lipa, 29, apparently happened, sparking rumours they were spotted dancing flirtatiously and that he even kissed her at the after-party. A source told the Sun, which published pictures of them together at the time: "There was no denying the chemistry between them. Jack was grinning from ear to ear as they chatted together and Dua clearly loved the attention.
"She couldn’t stop giggling as Jack nestled his head in her neck to give her a cheeky kiss. Dua kept rubbing her body against his as they closely danced together - with the pair even holding hands." However there were no further sightings of them together and speculation quickly died down.
It was a busy year for Jack in 2018 it seems as he was also linked to Scottish TV presenter and mum of two Kirsty Gallagher, after they met while co-starring on A League of Their Own. Onlookers reportedly saw them flirting at a party at London's Groucho Club before moving on to a friend's flat in the early hours where they were said to enjoy a kiss. Both declined to comment at the time and nothing came of the connection.
Blogger Roxie Nafousi is said to have dated Jack before his relationship with Gemma. In 2014, Roxie congratulated Jack on his BAFTA win via Twitter and they were spotted out together.
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