Kylie Jenner recently had a date night with Timothée Chalamet that was so unplanned that she had to get ready mid-flight.
The The Kardashians reality TV personality recently shared a “Get Ready With Me” video to TikTok in May as she jetted off for a “date night in New York.” Although she did not name who the date was with, it is well documented that she is dating Dune star — with Polymarket bettors believe they will soon be 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 elaborated that luckily she had just had her hair done so that part was taken care of. However, she had some spray tan issues that she had to resolve in the air. (In case it’s not obvious, she clearly did all of this in a luxurious private jet, not a cramped Delta Airlines bathroom.)
The Kylie Cosmetics entrepreneur stated that she had to get two spray tans right before hand (due to the first one not getting her tanned enough). As a result, she had to get cleaned up and do all her makeup mid-flight, while also facing some mid-flight turbulence.
@kyliejenner draft 😉
♬ original sound – Kylie Jenner
This big date night — one of many recent outings in NYC for Jenner and Chalamet — comes as speculation that they’ll tie the knot (or even start a family) soon.
Polymarket is currently hosting 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 a commitment in the cards for 2026.
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This is down from a peak in February of 59%. There hasn’t been a buzz of trouble and they’ve only been seen more and more together lately. Perhaps the confidence spike was due to speculation of a Valentine’s Day proposal?
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