Kylie Jenner’s Dating History: A Look Back On Her Relationships – Hollywood Life

Kylie Jenner’s Romantic History: From Tyga To Travis Scott To Timothee Chalamet

Kylie Jenner's love life has kept fans talking for years —especially now that Travis Scott has seemingly dissed her new flame, Timothee Chalamet. Learn about Kylie's relationship history here.

Reading Time: 6 minutes
View gallery

  • Kylie Jenner has been in an in on-again, off-again relationship with Travis Scott since 2017; their last split was in Jan. 2023 again
  • Kylie and Travis share two children: daughter Stormi, born in Feb. 2018, and son Aire, born in Feb. 2022
  • Kylie began seeing actor Timothée Chalamet in April 2023

Kylie Jenner has made a name for herself as one of the richest and most influential celebrities in the world. She helps run a wildly successful beauty company, Kylie Cosmetics, plus spinoff brands Kylie Skin and Kylie Baby. Not to mention, she has two of the cutest kids in the world with Travis Scott: daughter Stormi and son Aire. And, of course, she is on one of the hottest reality shows in the world: Hulu’s The Kardashians.

Ever since Kylie came into her own on Keeping Up With The Kardashians, the young starlet has captivated audiences. Not only has she grown up right in front of fans’ eyes, but she’s also dated in the limelight. Now, we’re taking a walk down memory lane with a look back at Kylie’s dating history.

Cody Simpson

Kylie Jenner, Cody Simpson
Kylie Jenner and Cody Simpson reportedly dated for a few months in 2011 when they were 14 years old (Photo: RM/©2012 RAMEY PHOTO)

Cody Simpson was Kylie’s first brush with her personal life going very public outside of KUWTK. The two, who were both 14 years old at the time, seemingly started dating after officially meeting at the premiere of Breaking Dawn: Part 1 in Nov. 2011. Cody and Kylie had a cute, flirty moment when the future Kylie Cosmetics founder interviewed him at the premiere, calling the singer her “rumor boyfriend on Twitter.”

While rumors circulated that the two were an item, Us Weekly confirmed that the two were dating. “They are a couple,” a source shared with the outlet at the time. “They are so cute together.” The innocent romance, however, quietly fizzled out after a few months. Cody went on to date model Gigi Hadid and singer Miley Cyrus.

Jaden Smith

Jaden Smith, Kylie Jenner
Kylie Jenner and Jaden Smith kept their rumored romance on the DL in 2013 (Photo: IXOLA / BACKGRID)

Kylie has always enjoyed a strong friendship with Jaden Smith. Many may forget that they actually dated in 2013, as the young love was kept completely on the DL when they were together. In 2013, the entrepreneur even called Jaden her “best friend” when wishing him a happy birthday. Kylie also took Jaden as her date to big sister Kim Kardashian‘s wedding to Kanye West in 2014, where they were spotted “making out,” according to E! News.

It’s not clear why they broke up, but the two have remained friends and were even spotted in a group photo (seen here) at  Justin Bieber‘s 2018 wedding to Hailey Bieber. Jaden was seen at Kylie’s sister, Kendall Jenner‘s, 25th birthday bash.

Lil’ Twist

Lil Twist, Kylie Jenner
Kylie Jenner and Lil Twist seen at Mauro Cafe at Fred Segal Melrose Store in West Hollywood on November 23, 2013 (Photo: OPC/ZOJ/WENN/Newscom/The Mega Agency)

Kylie and Lil Twist had a rumored romance in 2013 after things went from flirty to friendly with Kylie and Jaden. While this potential romance wasn’t as widely known, it appears that the two went on just a few dates in 2013. Even after things seemingly fizzled out, Kylie and Lil Twist kept things flirty on Twitter. But their relationship never amounted to anything serious.


Kylie Jenner, Tyga
Kylie Jenner and Tyga had an on-again, off-again relationship from 2015-2017 (Photo: Andy Kropa/Invision/AP)

Kylie’s first major high-profile relationship came during her romance with Tyga. The rapper and mogul met at Kylie’s sweet sixteen. It wasn’t until years later when Kylie and Tyga officially started dating in August 2015 — around the time of Kylie’s 18th birthday. The two had an on-again, off-again relationship for roughly two years before officially calling it quits in April 2017. Although rumors swirled about potential reunions between the two — especially after Kylie was posted visiting Tyga’s recording studio when she was on a break with Travis — any inkling of a romantic connection they had left did not develop into anything.

In fact, following a report that the two met up at a recording studio, Kylie took to Twitter to shut down any further speculation. “The internet makes everything 100 times more dramatic than what it really is. There was no ‘2 am date with Tyga’. You see me drop two of my friends off at a studio that he happened to be at,” she tweeted on October 3, 2019.

Although they never dated again, Kylie already confirmed that she and her rapper ex have a sweet connection.  “There was absolutely not one thing wrong with me and T. He and I will always, always have a bond,” she said on her reality show, Life of Kylie.

Travis Scott

Kylie Jenner, Travis Scott
Kylie Jenner and Travis Scott were in a committed relationship from 2017-2019 (Photo: zz/Elaine Wells/STAR MAX/IPx)

April 2017 is when Kylie and Travis Scott’s love story began. The two were spotted at Coachella at the time and things quickly heated up between the two. Less than one year after the couple’s romance started, Kylie and Travis became parents to their first child, Stormi Webster, on Feb. 1, 2018. Throughout their two-year romance, the couple waded through rumors about a potential engagement, and in Jan. 2019, Travis seemingly alluded to a possible proposal!

“It got to a point where I was like, ‘I need [Kylie] with me to operate. She’s that one,’” he shared with Rolling Stone. “We’ll get married soon. I just gotta sturdy up — I gotta propose in a fire way.” Months after his profile with the outlet, those romantic plans came to a shocking halt when Kylie and Travis broke up at the end of September 2019.

But following their split, fans often wondered if the two would get back together. Rumors about a potential romance between Kylie and rapper Drake were even thwarted due to the mogul’s very close relationship with Travis. A source close to Kylie and Travis revealed EXCLUSIVELY to HollywoodLife that the former couple was trying to keep their relationship status “under wraps.” The pair quietly rekindled their relationship, and they welcomed their second child in Feb. 2022. After initially naming him Wolf Webster, Kylie changed it less than two months later. She revealed her son’s new name is Aire in Jan. 2023.

As of Jan. 2023, it was reported that the couple separated once again. “Kylie and Travis are off again, they were supposed to spend the holidays together, but she went to Aspen to be with her family and friends up there,”  a source told Us Weekly. “This has happened so many times before, they’re known to be on again off again, but always remain friends and great coparents.”

Timothee Chalamet

Kylie Jenner and Timothee Chalamet at Paris Fashion Week (Photo: TheRealSPW / MEGA / Laurent VU/SIPA/Shutterstock )

Kylie and the Dune star were linked at the beginning of April 2023 after a video began circulating of them speaking a Paris Fashion Week 2023. It was reported that Kylie’s car was spotted at Timothee’s Beverly Hills mansion and that they enjoyed a taco date after Kylie sent her driver to pick the actor up from an art show in Santa Monica.

Then, a person close to the new couple confirmed that they are in fact an item, but aren’t putting pressure on themselves. “They are keeping things casual at this point. It’s not serious, but Kylie is enjoying hanging out with Timothée and seeing where it goes,” the individual told  Entertainment Tonight. “It’s been really fun for her because it feels a lot different than her past relationships. It’s new and exciting for Kylie and she’s having a lot of fun.”

In July 2023, as Timothee and Kylie’s romance continued to heat up, Travis dropped his fifth studio album, Utopia. Fans immediately noticed that a song called “MELTDOWN” on the album seemingly dissed Timothée by mentioning Willy Wonka. Timothée, of course, played the beloved character in the Dec. 2023 remake of Willy Wonka & the Chocolate Factory.

“Wrappin’ the cheese, wrap around me ’cause I’ve got property,” Travis raps on the track, which features Drakeper Genius. “Chocolate AP [Audemars Piguet] and chocolate the Vs / got the Willy Wonka factory / Burn an athlete like it’s calories, find another flame hot as me, b****.”

Kylie and Timothée’s relationship has continued to progress. They were spotted kissing while attending a Beyoncé concert in Los Angeles on Sept. 4. Days later, the twosome sat together during an intimate dinner for New York Fashion Week, per videos circulating on social media.