Despite their busy schedules and multiple breakup rumors over the past three years, it appears that Chalamet, 30, and Jenner, 28, have certainly hit their stride.
For Kylie Jenner , it seems there are no lengths she won't go to spend a spontaneous date night with her boyfriend of three years, Timothée Chalamet .
Even if that means flying her $70 million private jet to New York City to sit courtside with him at the New York Knicks playoff game, only to return to Los Angeles just 24 hours later. Despite their busy schedules and multiple breakup rumors over the past three years, it appears that Chalamet, 30, and Jenner, 28, have certainly hit their stride.
From packing on the PDA during their recent basketball date to Chalamet publicly declaring his love for his 'partner' earlier this year, fans have gone so far as to speculate that an engagement is imminent. But Jenner and Chalamet's relationship wasn't always so 'solid,' according to multiple sources who spoke exclusively to the Daily Mail.
Instead, insiders have detailed the 'friction' they endured – and how Jenner has finally figured out how to maintain a lasting relationship with the Hollywood star. Kylie Jenner and Timothée Chalamet have reportedly been dating since 2023.
But sources told the Daily Mail their relationship wasn't always as 'solid' as it is right now Chalamet, 30, and Jenner, 28, enjoyed a date night courtside at the New York Knicks playoff game against the Philadelphia 76ers on May 6 'Kylie has learned what the secret is to her and Timothée's three-year relationship,' one source told the Daily Mail.
'She now lets him do his own thing. That was something she was uneasy with when they first started getting serious. That caused friction between them.
' Since the couple met in January 2023, fans have witnessed Jenner and Chalamet locking lips at a Beyoncé concert, attending award shows together and cheering on their favorite sports teams. However, things reportedly took a turn for the pair in late 2025 as Chalamet's work schedule ramped up with filming Dune: Part Three overseas and promoting his sports-drama film, Marty Supreme.
Last October, it was even reported that Chalamet nearly broke up with Jenner due to their opposing views on marriage and her desire for him to settle down. Then, when asked about Jenner during a December 2025 cover interview with Vogue, he told the magazine: 'I just don't have anything to say.
' But by January this year, it seemed the two had worked to rebuild their relationship. At the 2026 Critics Choice Awards, where Chalamet won the coveted best actor award for his performance in Marty Supreme, he closed out his acceptance speech by thanking his 'partner of three years' for her 'foundation' and, of course, uttered the three little words 'I love you.
' A source told the Daily Mail that Jenner has unlocked the 'secret' to maintaining a lasting relationship with Chalamet after overcoming some 'friction' A second insider added: 'Kylie was initially jealous that she wasn't spending enough time with him when he goes off filming... but now ... any of those previous jealousy or trust issues are just not a thing anymore' Fans of the couple may be wondering exactly what went down behind the scenes, as Jenner and Chalamet appeared happier than ever during their most recent public outing. The source explained that Chalamet finally expressed his boundaries to Jenner, including his need for 'space' from time to time.
'She was making him feel claustrophobic,' they said. 'She wanted to be around him all the time. That wasn't working for him. He's a person who needs his space and she wasn't giving it to him.
'He made no bones finally telling her about it. 'While he loves her, he needs his space. She totally gets it now and there are no more trust issues. They're in a great place.
Their relationship is more solid than it's ever been.
' A second insider added: 'Kylie was initially jealous that she wasn't spending enough time with him when he goes off filming, but now they talk to each other every day and every night when he is on set, and they hang out with each other often enough that any of those previous jealousy or trust issues are just not a thing anymore. ' It may also help that Jenner, whose personal life has been blasted on reality TV for the last two decades, has refrained from blasting him over her social media accounts.
Earlier this month, a separate insider told the Daily Mail that Chalamet told Jenner 'he didn't ever want to be a prop' in their relationship and 'wants to avoid falling into the trap of being known simply for who he is dating.
' So strong are the couple right now, that Chalamet is fully 'on board' with popping the question to Jenner sometime in the near future Read MoreEXCLUSIVE Insiders reveal Timothee Chalamet's list of life-altering demands to Kylie Jenner and looming 'trap' Notably, Chalamet has not appeared in a single episode of Hulu's The Kardashians since they started dating. Jenner has also kept content featuring Chalamet off her social media, where she has almost 400 million followers on Instagram and 60 million on TikTok.
Even her famous family initially helped conceal any trace of Chalamet from their public profiles. Last year, sleuthing fans spotted Jenner's half-sister Kim Kardashian, 45, had even gone so far as to blur out Chalamet's name from an Easter table setting. The Kylie Cosmetics founder also appeared to follow Chalamet's lead when she kept quiet about their relationship in an October 2025 cover shoot for ELLE.
'I think it's important to keep things to yourself,' she told the magazine. 'It's hard for me to make a decision by myself sometimes, so the opinion of the whole world… it can be tough. ' But with public declarations at awards shows, regular PDA at New York Knicks games and her sisters Khloe and Kim Kardashian recently talking openly about the couple on the Khloé in Wonderland podcast, the relationship appears to be fully in its stride.
'Kylie is confident that she's number one in Timothee's life now,' said our first source. 'She used to be insecure in the relationship and she was open about it. 'She's accepted he has friends and interests that don't always include her. ' Now, it may be only a matter of time before Jenner and Chalamet take their relationship to the next level.
Jenner and Chalamet sat courtside at the Knicks game on April 28 alongside Tina Fey, Ben Stiller and Christine Taylor At the Knicks game last week, the reality TV star raised eyebrows as she wore a massive pear-shaped diamond ring on her pinky finger. Although Jenner has worn the sparkler on multiple occasions, some fans wondered when they can expect an engagement ring from Chalamet.
Jenner shares eight-year-old daughter Stormi Webster and four-year-old son Aire Webster with ex-boyfriend Travis Scott, but the former couple were never married. A third source told the Daily Mail that Chalamet is fully 'on board' with popping the question to Jenner sometime in the near future.
'Nobody would be surprised if they got engaged soon,' they said. 'He refers to her to all their mutual friends as his partner. 'He is 100 percent on board and in love. He never spoke openly about any woman until he dated Kylie.
' The moment could be as imminent as this summer according to our second source who said Chalamet's beloved Knicks could influence his decision. 'If the Knicks actually win the title and get rings, don’t be shocked if Timmy suddenly feels a little more inspired to hand Kylie one, too,' they said. A championship parade in New York could turn into a very big year for commitments.
' The Daily Mail has contacted representatives for Jenner and Chalamet for comment. The couple's commitment to each other was even further evidenced when Chalamet's ultimate superfan, Simone Cromer – the 59-year-old woman behind the Club Chalamet fandom – announced she was done with the Dune star. Last month, Cromer suggested that Chalamet becoming increasingly more public with his girlfriend was behind her decision to disband the fandom and instead turn her attention to Heated Rivalry's Connor Storrie, 26.
'To deny the obvious is to be obtuse and bury your head in the sand,' she wrote on Instagram. 'This fan community is not the same as it was four years ago. The notable shift was exactly 12 months ago, and the clock started to tick. Basically, so much has changed from what we all initially signed up for that it doesn't resemble what lured us here in the first place.
' As for Chalamet, the actor had a coy response when asked during a February interview if he will ever get married. 'You're going to get me in trouble, man,' he said, before adding, 'Yes. Yes. '
Kylie Jenner Timothée Chalamet Conflicted Relationship Breakup Rumors Film Schedule Pressure To Settle Down Jealousy Four-Year Relationship Space Boundaries Solid Relationship Forthcoming Engagement
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