A brash, shallow and cosmetically enhanced reality star – and a brooding thespian known for his sensitive portrayals of complex individuals. How could they possibly connect on a deeper level? But since getting together after a fling at Paris Fashion Week two years ago, Kylie Jenner and Timothee Chalamet have confounded their critics. Legions of fans of the floppy-haired Oscar-nominee believe he is wildly unsuited to Jenner – and insist that she will thwart his meteoric rise.

But the couple are continuing to defy naysayers – with Chalamet, 29, even dropping disapproving friends for his love, 27. ‘Some of Timothee’s pals didn’t think it was smart to get involved with the Kardashian clan,’ a source tells the Daily Mail. ‘They sat him down and expressed their fears that despite his many awards and nominations, the industry wouldn’t take him seriously if he was linked to Kylie.’ But perhaps his famed talent for observing other people has allowed him to glimpse the real Jenner, a ‘self-made’ billionaire, who is often seen by many as little more than another cog in the Kardashian gravy-train.

Since getting together after a fling at Paris Fashion Week two years ago, Kylie Jenner and Timothee Chalamet have confounded their critics. (Pictured together at the Vanity Fair Oscars afterparty earlier this month).

Legions of fans of the floppy-haired Oscar-nominee believe he is wildly unsuited to Jenner -and insist that she will thwart his meteoric rise. ‘He knew from the beginning that it wasn’t just a fling with Kylie,’ our source said. ‘He not only decided not to listen to his friends, but to also cut ties.’ Their romance blossomed in January 2023, when they were both invited to attend a Jean Paul Gaultier show in the French capital. They are said to have connected over mutual friends, a shared taste in music and their similarly ‘goofy’ personalities.

That same year, they were then seen attending a Beyonce concert, the US Open and a Saturday Night Live afterparty following Chalamet’s hosting stint in the November. The actor was even spotted in the background of the annual Kardashian-Jenner Christmas Eve soirée. They snogged at the Golden Globes in January 2024 before repeating their love-in at this year’s ceremony. Jenner and Chalamet’s vastly different upbringings have fueled the uncertainty over their surprising romance. Jenner grew up surrounded by excess wealth as the youngest sibling of reality TV royals.

She came of age in front of the cameras and was afforded little privacy as her teenage tantrums and family struggles – including her reaction to father Caitlyn (née Bruce) Jenner’s transition – were aired to millions. What Kylie Jenner and Timothee Chalamet really said during ‘painful’ exchange at tennis match

Meanwhile, Chalamet was raised in a federally subsidized artists’ building in Manhattan with his journalist father Marc Chalamet, his dancer-turned-real estate agent mother Nicole Flender and his sister Pauline. Fame only started licking at his heels in 2017 after his critically acclaimed role in gay romance Call Me by Your Name. So it is perhaps no surprise that the Hollywood heartthrob is worried about how much privacy he’s willing to sacrifice. ‘He really only wants to be a headline with his work, not his relationship, so he can be apprehensive at times,’ a separate source said.

His unease was apparent last weekend when Jenner grabbed him and awkwardly attempted to steal a kiss as they posed for a picture at the BNP Paribas Open tennis tournament in Indian Wells, California. ‘He is very much in love with Kylie, but he does get a little shy with PDA as he knows eyeballs are watching,’ said another insider.

Dating a Kardashian-Jenner is no easy feat, with Kylie’s ex-boyfriend, Australian singer Cody Simpson, previously saying: ‘The whole K-O-D-Y thing didn’t really work out for me.’ (Associates of the Kardashians often see new nicknames beginning with ‘K’. Chalamet’s new relationship has been given the portmanteau ‘Kylothee’).

Their romance blossomed in January 2023 in Paris. That same year, they were then seen attending a Beyonce concert, the US Open (pictured) and a Saturday Night Live afterparty following Chalamet’s hosting stint in the November.

They snogged at the Golden Globes in January 2024 before repeating their love-in at this year’s ceremony (pictured).

‘He really only wants to be a headline with his work, not his relationship, so he can be apprehensive at times,’ a source said. Sources previously told the Daily Mail that the actor was uncomfortable with the coverage of their PDA-heavy display at the Golden Globes last year and feared it could distract from his film, Dune 2, which he was promoting at the time. ‘Their kiss took away from the reason he was there,’ said a source. ‘His career is taking off and he wants to protect it and let it thrive based on his talent – not who he is or isn’t dating.’ But the pair weathered his unease and now ‘spend every waking second together.’ ‘What they have is real, despite what the naysayers believe,’ our insider insisted. Chalamet appears to have broken Jenner’s string of unstable relationships.

She had an on-again/off-again romance with rapper Tyga, who was 24 to her 17 years when they started dating in 2014. Three years later she moved on with fellow rapper Travis Scott, with whom she has daughter Stormi, seven, and son Aire, three. Like Tyga, theirs too was on-off. They finally called it quits in 2023 amid rumors of infidelity. It was not the first time that he had reportedly strayed, but Scott has denied cheating. If recent reports are to be believed, Chalamet could be gearing up for the long haul.

‘Her kids are super close with Timothee,’ our insider said. ‘And if he is now preparing to propose, she would say yes in a heartbeat.’