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Met Gala 2025: Kendall Jenner Steals the Show in NSFW Business Attire
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.
Kylie Jenner/Instagram
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.
Kylie Jenner/Instagram
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...
Kevin Mazur / MG23 / Getty Images for The Met Museum / Vogue / Rocco Spaziani / Archivio Spaziani / Mondadori Portfolio via Getty Images)
Romance Rumors: April 2023
Kylie Jenner and Timothée Chalamet first sparked romance rumors in April after her split from Travis Scott, with whom she shares kids Stormi, born in 2018, and Aire, born in 2022.
Matt Baron/BEI/Shutterstock, Karwai Tang/WireImage
Going Strong: August 2023
E! News confirmed in August that the Kardashians star and the Dune actor were still an item, despite reports claiming they’d called it quits.
Instagram / Gaia Repossi
Making It Official: September 2023
After packing on the PDA at Beyoncé's birthday concert in Los Angeles on Sept. 4, the pair attended a star-studded New York Fashion Week dinner together.
Sarah Stier/Getty Images
Doubles Partners: September 2023
Tennis is fine.
Gotham/GC Images
Courtside Kiss: September 2023
It was love-all at the US Open on Sept. 10.
Gotham/GC Images
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."
Dimitrios Kambouris/Getty Images for WSJ. Magazine Innovators Awards
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 award ceremony.
Gotham / GC Images
Live From New York: November 2023
...it's Kylie and Timothée. The pair arrive separately at the SNL after-party after the actor hosts the show.
Christopher Polk/Golden Globes 2024/Golden Globes 2024 via Getty Images
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.
Christopher Polk/GG2025/Penske Media via Getty Images
Make It a Tradition: January 2025
For the second straight year, Kylie was Timothée's date to the Golden Globes. The actor scored a nomination for Best Actor in a Motion Picture—Drama for his performance as Bob Dylan in A Complete Unknown.
Dave Benett/VF25/WireImage for Vanity Fair
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.
Allen Berezovsky/Getty Images
Having a Ball: April 2025
The duo enjoyed a night out at the Los Angeles Lakers vs. the Minnesota Timberwolves game in L.A.
Vittorio Zunino Celotto/Getty Images
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.
Brian Babineau/NBAE via Getty Images
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.
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