Jack Whitehall's wild flings before settling down with Roxy Horner

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Jack Whitehall's wild flings before settling down with Roxy Horner

Despite his somewhat geeky on-stage persona, Jack Whitehall has won over the hearts of many beautiful and talented women, including, according to reports, US heiress Paris Hilton.

Brit Awards 2025 host Jack, 36, has been in a serious relationship with his "life partner", the 33-year-old British model Roxy Horner, since 2020. The pair met in Australia when the comedian was touring and despite him taking the vegan star to a restaurant with dead ducks hanging on the walls and a bar decorated with taxidermed animals for their first date, they've been together ever since.

They grew closer rapidly during the COVID-19 pandemic when Roxy moved into the British star's Notting Hill pad where they spent lockdown together.

The surreal experience meant they got to know each at a much quicker pace than they would have done if they had been dating conventionally. Jack previously spoke about the odd effect it had on them. "Weirdly that was quite nice because we spent a lot of time together and it accelerates the relationship in a way," he said. "Then when lockdown ended, there was a lot of things we realised. We'd never gone to see a film together. We'd never been to a restaurant in England because we met in Australia."

After restrictions were lifted they made up for lost time back out in the real world and in May 2023 the couple announced they were expecting their first child together. They took to social media to share the happy news, posting a black and white photo of them holding an ultrasound of their unborn daughter. "And I thought I wasn't getting enough attention when the dog arrived..." Jack captioned the post, referring to the adorable rescue cavapoo he adopted with Roxy in 2021.

In September 2023 they announced the birth of their first child Elsie and in December last year, Roxy shared on Instagram that she and Jack were engaged. The self-confessed "man-child" shared his struggles to adapt to life as a responsible father and partner in his 2023 stand-up tour Settle Down.

He told the Scottish Herald at the time what the show was about: "I've met my life partner and we've moved in together and we’ve got the house, the mortgage and the dog," he said. "Very grown up things and I feel like I'm edging into a new phase in my life. And it's all about my sometimes reluctant acceptance of that and my growing old disgracefully."

Before his adult phase though, the funnyman was quite the lothario with a long list of rumoured flings under his belt. According to The Sun, in May 2019, Jack and lingerie model Melinda London had dinner together at exclusive private members club White City House in London's Shepherd's Bush. Melinda had recently split from DJ and producer Jonas Blue after dating for two years. Neither Melinda nor Jack confirmed anything at the time.

One very unlikely flame 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 which is where his dalliance with pop star Dua Lipa, 29, apparently started. Rumours swirled that 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 the rumour mill 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.

Before his numerous flings, Jack was in a long term relationship with Humans actress Gemma Chan. The pair met on the set of the E4 sitcom Fresh Meat in 2011, after the Crazy Rich Asians star was cast as Kingsley's love interest, Ruth. In 2013, Kent born Gemma, 42, revealed that she and Jack went to Nando's for their first date after hitting it off behind-the-scenes. The couple went on to live together in Notting Hill, not too far from the comedian’s family home. They split in 2017, however, after six years. It was initially reported that the couple separated because of their hectic work schedules, but Jack would later reveal that the break-up was spurred by disagreements on having children.

"I've had a lot of changes in my life recently," he told the audience at one of his stand-up gigs in 2018, according to The Express. "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." He went on to claim that Gemma "wanted kids" while he "wanted to escape," before admitting to not being good with kids.

Jack joked about how frustrating their amicable split was. "You want to hate the person, that is a healthy way to end a relationship," he said. He also revealed bad break-ups were good material for his stand-up shows. "She couldn’t even do that," he quipped. "No one has ever written an album about a wonderful break up where everyone behaved impeccably." In 2018 Gemma moved on with Marvel star, Dominic Cooper and the pair are still together.

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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