Kylie Jenner 'Genuinely Loves Spoiling' Timothée Chalamet, As She Picks Up The Tab During Romantic Getaway

By Favour Adegoke on January 31, 2026 at 8:15 PM EST

Timothée Chalamet And Kylie Jenner at the Marty Supreme Los Angeles Premiere
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Kylie Jenner and Timothée Chalamet's relationship continues to heat up, with sources recently spilling about the couple's romantic getaway to Mexico.

According to a report, the Oscar-nominated actor "looked completely smitten" with the reality TV star, who was more than happy to pick up the tab on their date nights.

This comes amid rumors that Timothée Chalamet and Kylie Jenner are more serious than ever and are even discussing a possible engagement this year.

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Inside Kylie Jenner And Timothée Chalamet's Ultra-Romantic Getaway To Mexico

Timothee Chalamet And Kylie Jenner In Rome, Italy
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Sources recently revealed to journalist Rob Shuter's #Shuterscoop that Kylie gladly picked up the tab on date nights with Chalamet during their Mexico getaway.

The power couple was seen hand in hand at Flora Farms in Cabo San Lucas, with witnesses claiming the vibe between them was very affectionate.

"Timothée looked completely smitten," a source noted. "He was taking photos of Kylie the entire time — like a proud boyfriend on vacation."

The duo is said to have enjoyed a laughter-filled dinner, with Kylie particularly taking her time to savor the farm-to-table delicacies. "Kylie covered everything," another source revealed. "Dinner, travel, the whole experience. She genuinely loves spoiling him."

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Wedding Bells Reportedly On The Horizon For Kylie Jenner And Timothée Chalamet

Timothee Chalamet and Kylie Jenner at the Marty Supreme Los Angeles Premiere
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Wedding bells might also be on the horizon for Kylie and Chalamet, as an insider who spoke to Us Weekly revealed that the couple has "talked about getting engaged this year."

According to the insider, "Kylie definitely runs the show, and Timothée loves it. It is a great balance between both of their personalities, and it works."

Although they began dating quietly in early 2023, the pair has stepped into the spotlight more often lately.

They made waves late last year when they appeared in matching orange leather looks at the premiere of Chalamet's film "Marty Supreme."

Then, at the Critics Choice Awards, Chalamet notably acknowledged their relationship while accepting his award for Best Actor.

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"Lastly, I would like to thank my partner of three years," the actor said. "Thank you for our foundation."

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Timothée Chalamet Steals Hearts Of Kylie Jenner's Kids And Family

Timothee Chalamet And Kylie Jenner In Rome, Italy
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Sources say the relationship has been a refreshing change for Kylie. She and Chalamet reportedly have an "easy, chill relationship," and spend most of their time together.

When Kylie is in the city or doesn't have her kids with her, she often stays at Chalamet's place, while he regularly visits her home as well.

The "Wonka" star has also become part of Jenner's family life and has met her children, Stormi, 7, and Aire, 3, whom she shares with Travis Scott.

While Kylie took her time before introducing her kids to the movie star, insiders say the transition has been smooth, and the children have grown very fond of him.

The warmth extends to the rest of the Kardashian-Jenner family as well. Chalamet is reportedly welcomed at family gatherings and holidays and is included in their plans.

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"They all really like him for her and think he has brought out a softer side to Kylie. … She lights up when she talks about him and is always his biggest cheerleader," the insider added.

Khloé Kardashian Praises Timothée Chalamet's Bond With Kylie Jenner

Kylie Jenner and Timothée Chalamet court side at the Knicks vs Pacers Game 5
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Kylie's sister, Khloé Kardashian, recently offered a glimpse into how well Chalamet fits in with their family during an episode of her podcast, "Khloé in Wonderland."

She recalled a small, intimate dinner in Malibu with about a dozen guests, describing it as relaxed and fun. Kylie, she noted, arrived first and stayed until the very end of the night.

The "Revenge Body" alum added that Kylie and the "Call Me by Your Name" actor clearly enjoyed themselves, saying the couple had an amazing time together and left a great impression on everyone there. "I was so proud of her," she noted.

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Caitlyn Jenner Has Given The Actor Her Stamp Of Approval

Timothee Chalamet and Kylie Jenner at Lakers Vs. Timberwolves - Game 5
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Approval of Kylie and Chalamet's romance has also come from Caitlyn Jenner, who recently weighed in on the relationship while speaking to TMZ.

She emphasized that Kylie's happiness is what matters most to her, adding that Chalamet seems like a genuinely good person.

Caitlyn praised the movie star as a "phenomenal actor and a good kid," who treats the Kylie makeup mogul well.

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