Red Flags In Kylie Jenner And Timotheé Chalamet's Relationship

Kylie Jenner and Timotheé Chalamet met at the Jean Paul Gaultier fashion show in January 2023, shortly after Jenner split from partner Travis Scott. Romance rumors between the two started circulating in April of that same year, only to amplify every time they were seen at the same event. From attending Beyonce's birthday concert in September 2023, to showing PDA at the U.S. Open, it became pretty evident to the world that the two had become a couple.

While we love love and want to see a public romance succeed, there's no denying that Jenner and Chalamet have made strong efforts to keep their relationship private. On the one hand, that's completely understandable; many public figures don't want to face endless scrutiny about their private life. On the other hand, too much privacy can run the risk of stunting the romance. Women.com spoke with Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, to get her expert take on the relationship between these two A-listers. As Trombetti told us, there are more than a few red flags when it comes to the young Hollywood couple.

Kylie Jenner and Timotheé Chalamet have not walked the red carpet yet as a couple. Although Jenner and Chalamet sat next to each other at the 81st Golden Globes in January 2024, they didn't walk in together. Instead, they arrived, each in a black outfit, separately. In November 2023, Jenner arrived at SNL in New York City to support Chalamet as he hosted the evening. However, they arrived individually. Jenner also supported Chalamet by secretly attending his premiere of "Wonka" in December 2023 with her mother, Kris Jenner. The two women arrived at the Regency Village Theatre in Los Angeles to no fan-fare, opting instead to discretely slip into the theatre once the movie began. 

While they may wish to give the other their moment and not have their romance distract from the event, Susan Trombetti told us that this was concerning nonetheless. "I can see not doing it early on, or when he has a movie premiere," Trombetti told us of Jenner and Chalamet. "Especially when it's some of his own projects, you don't want the relationship to overshadow his premiere. At this point though, it's strange. We know they are together, so why not walk the carpet at the Golden Globes? I don't get it." At this point, we'll have to wait and see whether Jenner makes an appearance at Chalamet's next premiere.

Kylie Jenner and Timotheé Chalamet have waded through breakup rumors more than once during their relationship. In August 2023, Life & Style reported that Chalamet broke up with the cosmetics mogul. This happened again in March 2024, when Jenner avoided a question about her relationship during an interview with The New York Times. The outlet asked if Chalamet was influencing Jenner's fashion, which has notably become more subdued since dating the "Dune" star. "I don't know how I feel about that," Jenner said. "I just don't want to talk about personal things." Because of this response, fans assumed that the pair called it quits. 

While the rumors have either been false, or the couple has reunited after breaking up, Susan Trombetti sees this as troubling. "It seems he has broken up with her before, early on, and that's when you should be all in during those early stages," Trombetti told Women.com. "It's those rose colored glasses that keep you crazy about each other, so if it's to be believed, why is he breaking up with her?" It certainly seems worrying. As Trombetti noted, where there's smoke, there's frequently fire, especially when it comes to celebrity relationship rumors. And if Chalamet has broken up with Jenner before, this can pose threats to their longterm happiness. After all, on-again, off-again relationships can cause more harm than we initially realize. 

While there have been sightings of Kylie Jenner and Timotheé Chalamet from their first romantic link in 2023, there have been long spells when the two aren't spotted together at all. As Susan Trombetti noted to Women.com, the two weren't photographed from their evening together at the 2024 Golden Globes in January until the end of June. There certainly is an argument for privacy. After all, Jenner did keep her first pregnancy, with daughter Stormi, a total secret from the world. 

However, a relationship is a more dynamic thing that involves two people interacting, and Trombetti felt like this is a red flag. "Either they have been great at evading the paps, or they weren't seeing that much of each other if at all," she told Women.com. "It's all very speculative, but you get the point. These two didn't seem to be hanging out much, but perhaps they had projects keeping them apart." So the fact that they weren't seen at all together, even with paparazzi hanging around at every opportunity, seems to be a problem, and as far as Trombetti thinks, they weren't connecting that much in person. While interdependence in a relationship is a very healthy thing, too much alone time can wear a couple down. 

Family opinion is everything, and this seems to certainly be the case for the very close Kardashian-Jenner clan. So rumors of familial disapproval around Kylie Jenner and Timotheé Chalamet's relationship would be a huge problem. In July 2024, Life & Style sourced an insider, who said that the Kardashians were not fans of Chalamet's. The outlet claimed that Chalamet was making no effort to get close to Jenner's family, and ignores them when he was at family events. The insider even said that Chalamet acts like the reality stars are beneath him. 

Noting that this information was not confirmed by Jenner herself, Susan Trombetti told Women.com that this detail has the potential to be a major red flag. "If it's true, sometimes you just have to believe friends and family," Trombetti told us. "It's like dogs and small children. Pay attention when they don't like someone you are dating. The family is said to not like that he doesn't spend time with them, and they feel he doesn't put in a lot of effort with Kylie. He should be proving himself to her, so why the distance?" No doubt the Kardashians and Jenners are trying to spare Kylie from Chalamet treating their connection as a backburner relationship, where he's just keeping her around as an option but doesn't see it as something serious. 

Though it might seem trivial, the fact that Kylie Jenner and Timothée Chalamet haven't gone Instagram official is a worrying sign. In the era of social media, posting a relationship is a way of securing it, of making it official, and proudly owning it. The fact that both Gen-Z stars remain active on Instagram without acknowledging this part of their life seems unusual. After all, their relationship is already widely-spread news, and wouldn't come as a shock to anyone, so there really isn't a need to be hesitant about sharing it. 

For Susan Trombetti, this is a red flag. Even worse, it speaks to a possible ambivalence about the relationship. "So, it's kind of childish, but in the Kardashian world where they are so big on social media, it's kind of a big deal!" she told Women.com. "We know they are dating, so why not ? Who knows what their story is? But they don't seem to be claiming each other. They certainly don't need to explain, but as a matchmaker, they don't come off as passionate about each other." Our only hope is that both Jenner and Chalamet find their happiness. They're both remarkable people, and if they choose to stay together, we'll ship them to high heaven. But if the red flags start to pile up, it might be worth it to find love with other partners.