Kylie Jenner’s Dating History Is More Complex Than Any of Her Sisters

Kylie Jenner
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Of the five Kardashian-Jenner sisters, Kylie Jenner’s dating history is the most complex. Sure, sisters like Kendall Jenner and Khloé Kardashian have had more obscure NBA boyfriends, but there’s something about Kylie’s relationship past that seems much more interesting. Perhaps it’s because she’s the youngest of the Kardashian-Jenners, and therefore is the most public about her relationships. Of the sisters, Kylie has probably posted the most her boyfriends on Instagram. Heck, she even confirmed when she and Travis Scott broke up (more on that later) in 2019 days after the news broke.

But before we dive into Kylie’s ~celebrity~ boyfriends, let’s look back at the first-ever BF we know of: a man named Ramsey IV. According to Cosmopolitan, Kylie and Ramsey IV dated from 2008 to 2011 when she was just 12 years old. The two were in middle school at the time, and Ramsey IV even confirmed the relationship in his Instagram comments. (It was truly a different time back then.) “I love her (:” he responded to a fan at the time who asked if he and Kylie were dating. It’s unclear how the relationship ended, but Ramsey IV is by far Kylie’s least-known relationship. Find out the rest of her relationship history ahead.

Cody Simpson (2011)

Kendall Jenner, Gigi Hadid, Cody Simpson

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Before Cody’s relationships with Gigi Hadid and Miley Cyrus, he dated Kylie. The two, who were both 14 at the time, met at the premiere of Breaking Dawn: Part 1 in November 2011. At the premiere, where Kylie and Kendall interviewed Cody, the Kylie Cosmetics founder even joked about how fans shipped them together. “You’re my rumor boyfriend on Twitter,” Kylie said to Cody. “Nice to finally meet you.” Fast forward a few weeks later, and Us Weekly reported that the two actually became a couple. . “They are a couple!” a source told the magazine at the time. “They are so cute together.”

However, the relationship didn’t last more than a couple months. In an interview on Hello Ross in 2014, Cody joked about how the two broke up because his name didn’t start with the letter K. “The whole K-O-D-Y thing didn’t really work for me,” he said.

Jaden Smith (2013)

Kylie Jenner, Jaden Smith

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Kylie and her former best friend Jordyn Woods have Jaden to thank for their friendship. Jaden, who introduced Kylie and Jordyn, dated the Kylie Skin CEO on the DL in 2013. The two confirmed their relationship when Kylie took Jaden as her date to Kim Kardashian and Kanye West’s wedding. Kylie and Jaden were also seen making out at the reception, according to E! News. After their breakup, the two remained friends. There was also some drama involving Jaden and Kylie’s then-boyfriend Tyga, who was jealous of the reality star’s friendship with Jaden when Kylie and Tyga dated in 2015.

“Kylie and Jaden have been hanging out lately and it made Tyga suspicious. He thought something might be going on. So that was one issue,” a source told E! News at the time. “She has a close relationship with Jaden since they were very young but nothing romantic has happened with them since she has been with Tyga. Jaden though will always love Kylie and Kylie will always have a love for Jaden. They grew up together and were each others’ first loves.

Lil Twist (2013)

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Rapper Lil Twist and Kylie had a short-lived romance in 2013. According to TMZ, the two went on a date only a week after Kylie and Jaden went to the movies together. They’ve also flirted a little on Twitter, as seen in the below tweet where Lil Twist dropped the L bomb on Kylie who responded with a slew of emojis.

Tyga (2014 – 2017)

Kylie Jenner, Tyga

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Ah, Tyga. Before her relationship with Travis Scott (who we will get to later), Tyga was Kylie’s most public and significant boyfriend. The two met at Kylie’s Sweet Sixteen in 2011 where he performed. Though there were rumors that the two started dating soon after, Tyga denied the claims. “DONT BELIEVE THE RUMORS, BEEN FRIENDS WITH THE FAMILY FOREVER. WERE ALL JUST FRIENDS,” he tweeted in 2014.

Because of Kylie’s age at the time of the rumors, Tyga received a lot of heat, especially from Amber Rose, who is best friends with Tyga’s ex Blac Chyna. “[He] should be ashamed of himself. That’s how I feel. For sure…he has a beautiful woman [Blac Chyna] and a baby and left that for a 16-year-old who just turned 17. Like, nah,” Amber told a radio station at the time.

Tyga and Kylie finally confirmed their relationship in August 2015 after the reality star’s 18th birthday. They dated on and off for a couple more years before their official split in April 2017. Since their breakup, Tyga has remained mum on his relationship with Kylie. Reunion rumors sparked between the two in 2019 when Kylie was seen with Tyga days after her split from Travis Scott. Kylie took to Twitter to deny the claims, explaining that it was simply a coincidence that the two were at the same hotel.

Party Next Door (2016)

PartyNextDoor

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Kylie dated Party Next Door for some time in between her on-again, off-again relationship with Tyga. Rumors first flew when the two made out in his 2016 music video for “Come and See Me.” Kylie told Complex in 2016 that the two dated but were never in an official relationship.

“Me and Party have a cool relationship. I think he’s so talented and I love his music,” she said at the time. “But I wouldn’t say we dated. It never really got to that boyfriend-girlfriend stage. It was just fun. I was doing what I wanted to do.”

Travis Scott (2017 – 2019)

Kylie Jenner, Tyga

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Kylie and Travis’ love story started in April 2017 when they were seen making out at Coachella. Fast forward to February 2018, and the couple welcomed their first child, a daughter named Stormi Webster. Throughout their two-year relationship, Kylie and Travis fielded rumors about their “secret” engagement. Travis responded to the rumors in January 2019, telling Rolling Stone that he planned to propose to his then-girlfriend. “It got to a point where I was like, ‘I need [Kylie] with me to operate. She’s that one,’” he said. “We’ll get married soon. I just gotta sturdy up — I gotta propose in a fire way,” he said at the time.

That plan came to an end when Kylie and Travis split in September 2019. A source told People at the time that there “several issues” for the breakup, but one of the main one was the couple’s disagreement on having a second baby. “There were several issues that made them want to take a break,” the insider said. “Kylie is all about family and really wants a second baby.”

The two have remained friendly since their split though. Travis even spent Thanksgiving with Kylie and Stormi at Kris Jenner’s house in 2019. Because of their closeness, rumors have flown that the two are back together, but neither Kylie nor Travis have confirmed the reunion.

Drake (2019)

Drake

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Drake, who’s known the Kardashian-Jenner family for years, and Kylie had a short-lived romance at the end of 2019 after her split from Travis. A source told Us Weekly in October 2019 that the two flirted at Drake’s 33rd birthday party. Kylie and Drake’s friendship did take a romantic turn recently,” a source told Us Weekly at the time. “They’ve been seeing each other romantically.”

An insider also told HollywoodLife at the time that Travis would feel a “bit betrayed” if anything romantic happened between Kylie and Drake, given that the rappers are good friends. Drake’s flirtmance with Kylie didn’t last long though. A source told HollywoodLife in December that Drake ended things with Kylie because he saw her more as a friend. “Drake has definitely moved past any type of romantic feelings towards Kylie and it’s purely platonic between them at this point,” the insider said. “There were absolutely some flirtations going on from Drake towards Kylie a while back. [It] was all in good fun, and there was nothing really serious that came out of it.” Welp.

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