Kendall Jenner’s sister trip to New York may have been a slam dunk—but it wasn’t without its hiccups.
Indeed, days after Kylie Jenner and Kendall join Timothée Chalamat in watching the New York Knicks take on the Boston Celtics at Madison Square Garden May 12, Kylie shared a pic of their private jet flight to the Big Apple, during which the model chipped her front tooth.
In the clip posted to Instagram May 13, the two sisters are heard laughing as the Kylie Cosmetics founder films Kendall sitting in her seat as she zooms in on something white on her fingertip.
One of them says, “Did my nail come off, or was it my tooth?” Before Kylie proclaims, “B—h, you are not going to the Knicks game today!”
The Khy founder—who shares kids Stormi, 7, and Aire, 3, with ex Travis Scott—then brings the camera closer to Kendall’s teeth, which showed that one of her front two teeth had indeed chipped off.
After one of Kylie’s kids, who joined them on the flight, asks “what?” off camera, she replies by saying, “Kendall’s tooth fell off!”
Throughout the whole ordeal, the 818 Tequila founder could be heard hysterically laughing, so she clearly took the mishap in stride—and she did end up going to the Knicks game.
Elsewhere in Kylie’s Instagram carousel post documenting their trip, Kylie and Kendall posed in Knicks hats and matching leather pants and cheered on the basketball team after their big win. Kylie also shared a video of Stormi helping Aire open a tray of fried chicken in their hotel room, a couple of selfies and more.
The sister duo made headlines by sitting front row at the basketball game with Kylie’s boyfriend Timothée. While he didn’t appear in any of his girlfriend’s social media activity documenting her trip to New York, he did sit between Kylie, 27, and Kendall, 29, during the game, which signaled to many that their relationship has the approval of Kylie’s older sister.
The rare high-profile outing for the couple—who started dating in 2023—came after Timmy and Kylie recently made their red carpet debut as a couple at the 70th David di Donatello award ceremony in Rome.
When the A Complete Unknown star, also 29, was honored a Special David prize for his achievements in acting during the award show, he shared a kiss with Kylie before taking the stage to accept his prize.
Despite the back-to-back public outings, Kylie and Timothée have remained extremely tight-lipped about their romance as it continues to blossom.
One person who has spoken about their relationship? The Wonka actor’s mom.
“I have to say she’s lovely,” Nicole Flender told Curbed in an interview published April 21. “She’s very nice to me.”
Keep reading for more about Kylie and Timothée’s relationship…
Romance Rumors: April 2023
Kylie Jenner and Timothée Chalamet first sparked romance rumors in April 2023 after her split from Travis Scott, with whom she shares kids Stormi, born in 2018, and Aire, born in 2022.
Going Strong: August 2023
E! News confirmed in August 2023 that the Kardashians star and the Dune actor were still an item, despite reports claiming they’d called it quits.
Making It Official: September 2023
After packing on the PDA at Beyoncé‘s birthday concert in Los Angeles in September 2023, the pair attended a star-studded New York Fashion Week dinner together.
Doubles Partners: September 2023
Later that same month, the couple attended the U.S. Open in New York.
Courtside Kiss: September 2023
It was love-all at the US Open in September 2023.
Desire for Private Life: October 2023
When Kylie’s level of fame was brought up during Timothée’s recent discussion with GQ about privacy, he responded with a laugh.
“This reminds me of that recent South Park episode with the Worldwide Privacy Tour,” he said, referencing the show’s parody of Prince Harry and Meghan Markle. “Sometimes, people are going to be hella confused when you say you’re trying to live a private life.”
WSJ. Magazine 2023 Innovator Awards: November 2023
Though the two skipped walking the red carpet together, they were all smiles on their date night to the 2023 award ceremony.
Live From New York: November 2023
…it’s Kylie and Timothée. The pair arrived separately at the SNL after-party after the actor hosted the show in November 2023.
Table for Two: January 2024
What award show?
It was only lovers in the building as the 2024 Golden Globes doubled as a TImothée-and-Kylie kiss cam. And there was nary a rumor that could puncture their blissful bubble.
Make It a Tradition: January 2025
For the second straight year, Kylie was Timothée’s date to the Golden Globes 2025. The actor scored a nomination for Best Actor in a Motion Picture—Drama for his performance as Bob Dylan in A Complete Unknown. Though he ultimately lost to Adrien Brody, he won in the romance category with Kylie.
Vanity Fair: March 2025
While Kylie did not join Timothée at the 2025 Oscars, where he was nominated for his role as Bob Dylan in A Complete Unknown, she was by his side at Vanity Fair‘s after-party.
Having a Ball: April 2025
The duo enjoyed a night out at the Los Angeles Lakers vs. the Minnesota Timberwolves game in L.A. in April 2025.
Red Carpet Debut: May 2025
The couple walked their first red carpet together at the 70th David Di Donatello award ceremony in Rome, where Timothée was honored with a special prize for his acting.
Keeping Up With Family: May 2025
Kylie’s sister Kendall Jenner joined the pair on their date at the New York Knicks vs. Boston Celtics game at Madison Square Garden in N.Y.C.
Romance on Set: August 2025
Kylie took a trip to Budapest in August 2025 to visit Timothée while he was filming Dune: Part Three. The couple posed for photos with fans during a trip to a local coffee shop.
