Kylie Jenner recently had a date night with Timothée Chalamet that was so unplanned that she had to get ready mid-flight.
The Kardashians reality TV personality recently shared a “Get Ready With Me” video on TikTok in May as she headed out for a “date night” in New York. Although she did not mention who the date was with, it is well documented that she is in a relationship with the Dune star — with Polymarket gamblers believing that they will soon become engaged.
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Jenner, 28, said the big night was “very last minute” and the whole trip would be a whirlwind 24 hours. She said that luckily she had just had her hair done, so that part was taken care of. However, she had some issues with spray tan that she had to solve on air. (In case it’s not obvious, she clearly did all of this on a luxury private jet, not in a cramped Delta Airlines bathroom.)
The Kylie Cosmetics entrepreneur said she had to get two spray tans right beforehand (because the first one didn’t tan her enough). As a result, she had to clean up and put on all her makeup mid-flight, while also dealing with some mid-flight turbulence.
@kyliejenner concepts 😉
♬ original sound – Kylie Jenner
This big date night — one of several recent New York outings for Jenner and Chalamet — comes amid speculation that they will tie the knot (or even start a family) soon.
Polymarket is currently organizing a market for “Kylie Jenner and Timothée Chalamet engaged in 2026?”, which has a simple yes/no binary. The market believes there is a 21% chance of an engagement in the cards before 2026.
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This is down from the peak of 59% in February. There have been no problems and they have only been seen together more often lately. Perhaps the spike in confidence was due to speculation about Valentine’s Day proposals?
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