Kylie Jenner’s Complete Dating History
Timothée Chalamet was most recently linked to Kylie Jenner following her breakup with Travis Scott, the father of her two children.
Kylie Jenner started dating rapper Tyga when she was a teenager. He gave her expensive gifts, like a Ferrari and a promise ring, but they broke up in April 2017.
Right after, she started dating Travis Scott. They had a baby named Stormi less than a year later. They even did a photoshoot for Playboy where Kylie talked about being a sexy mom.
They took a break but got back together and had a baby boy in February 2022. However, they split up again less than a year later.
People think they might get back together again because they’ve broken up before. Now, Kylie might be dating actor Timothée Chalamet.
1: Cody Simpson and Kylie Jenner
In 2011, there were rumors that Kylie Jenner was dating Australian singer Cody Simpson. But neither of them confirmed it. Years later, Cody Simpson joked about their relationship not working out, saying “the whole K-O-D-Y thing didn’t really work out for me” on E!’s Hello Ross show.
2: Tyga and Kylie Jenner
Jenner’s first serious relationship was with rapper Tyga. They met at Kendall Jenner’s 16th birthday party in November 2011, but they didn’t start dating until three years later.
Tyga hosted Kylie’s 17th birthday party at his house in August 2014, shortly after ending his engagement with Blac Chyna.
Initially, Tyga denied dating Kylie on a talk show, but later he gave her an expensive car and got a tattoo for her.
They broke up in May 2016 but got back together a few months later. In an interview, Kylie explained that she wanted to see what life was like without Tyga but realized she wanted to be with him.
They finally broke up for good in April 2017. In a TV show, Kylie mentioned there was nothing wrong with their relationship, but she felt she was too young to commit fully.
3: Jaden Smith and Kylie Jenner
Jenner never officially confirmed being in a relationship with Jaden Smith, but there were hints they were more than friends.
In April 2013, Smith mentioned spending time together in different places and called Jenner one of his best friends.
Jenner also posted a photo for Smith’s birthday, calling him her best friend and expressing gratitude for their connection. She mentioned how he understands her and always knows how to make her laugh.
4: Travis Scott and Kylie Jenner
Rumors of romance between Kylie Jenner and Travis Scott began when they were seen holding hands at Coachella in 2017. They started appearing together more often and even got matching tattoos early in their relationship.
In September 2017, it was reported that Kylie was pregnant with their first child, but she kept it secret until they announced the birth of their daughter, Stormi, in February 2018. They made their first public appearance after Stormi’s birth at the 2018 Met Gala.
In an interview for Playboy in 2019, they talked about their relationship and how having a baby didn’t affect their sexual life. They broke up in October 2019 but got back together in 2021.
In August 2021, they announced they were expecting their second child. Kylie gave birth to their son on February 2, 2022, the day after Stormi’s birthday. Initially named Wolf, they later changed his name to Aire.
However, they split up again less than a year after Aire’s birth. Despite this, sources suggest they might reconcile in the future, as they have different priorities but a strong connection.
5: Drake and Kylie Jenner
In 2019, following her breakup with Travis Scott, there were reports that Kylie Jenner was spending time with Drake. According to a source, they had been friends for a while, and Drake was close to her family.
One friend mentioned that Jenner and Drake had been flirting and hanging out since her split with Scott in October. However, other insiders insisted they were just friends.
Their interactions seemed to increase after Jenner attended Drake’s 33rd birthday party and his Halloween party shortly after. A source mentioned that she stayed “super late” at the Halloween party.
6: Timothée Chalamet
In April 2023, a source close to Kylie Jenner informed media outlets that she and Timothée Chalamet were “spending time together and getting to know each other.” Pictures of Jenner’s Range Rover in Chalamet’s driveway were previously shared by TMZ, and the duo were spotted interacting during Paris Fashion Week in January.
According to another insider, they meet up weekly, but their relationship isn’t serious. After her on-and-off relationship with Travis Scott, Jenner wants to date without pressure. The source mentioned that Jenner’s family supports her dating choices.
In May 2023, a different source close to Jenner stated that while she enjoys dating, her priority is being a mom. They noted that her involvement with Chalamet is casual.
Despite Travis Scott seemingly referencing Chalamet in his track “Meltdown” later that year, Jenner and Chalamet were seen sharing a kiss at a Beyoncé concert in September, suggesting they were still together.
In January 2024, an insider revealed that Jenner and Chalamet’s relationship has been uncomplicated and enjoyable. Chalamet encourages Jenner to focus on the present, which she appreciates. The source also mentioned that Jenner’s family, particularly Kris Jenner and Kim Kardashian, are supportive and optimistic about the relationship.
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