Kylie Jenner Triumphs Over Mid-Flight ‘Turbulence’ for ‘Last-Minute’ Timothée Chalamet Date Night

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 to TikTok in May as she jetted off for a “date night in New York.” While she didn’t name who the date was with, it is well-documented that she’s dating the Dune star — with Polymarket bettors believing they’ll become engaged soon.

Jenner, 28, said the big evening was “very last-minute” and the whole trip would be a whirlwind 24 hours. She detailed that she had luckily just gotten her hair done, so that part was taken care of. However, she had some spray tan difficulties she had to sort out mid-air. (In case it’s not obvious, she was clearly doing all this in a luxurious private jet, not a cramped Delta Airlines bathroom.)

The Kylie Cosmetics entrepreneur detailed she had to gotten two spray tans just beforehand (due to the first not making her tan enough.) As a result she had to get cleaned up and all her makeup done mid-flight, while also facing some mid-flight turbulence.

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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 currently hosting a market for “Kylie Jenner and Timothée Chalamet engaged in 2026?,” which has a simple Yes/No binary. The market believes there’s a 21% chance of an engagement in the cards for 2026.

This is down from a February peak of 59%. There hasn’t been an buzz of trouble, and they’ve only been seen more and more together lately. Maybe the confidence was spike was due to Valentine’s Day proposal speculation?

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