Hi, So Kylie Jenner’s Dating History Is Genuinely Shocking?

Kylie Jenner has been in a longtime on-again-off-again relationship with a billion dollars Travis Scott, but—much like the rest of us—she had to metaphorically swipe left on a lot of duds to find him, and low-key still is. No offense to anyone on this list, I’m sure you’re all great!

If you’ve been keeping up with the Kardashians, you already know that Kylie dated Tyga before she and Travis fell in love and welcomed their adorable kids Stormi and Aire to the world—but he’s just one of her ex-boyfriends. Like...DID YOU KNOW SHE DATED CODY SIMPSON? You do now. Let’s begin.

RAMSEY IV: 2008 to 2011

Never heard of Ramsey IV? That’s because he was Kylie’s boyfriend when she was literally 12. These two dated for a pretty long time (2008 to 2011!) considering they were—what?—in seventh grade?! They didn’t even have good selfie-taking skills yet, see?!!

If you truly don’t know how you missed this chapter in Kylie’s life, it’s because the relationship wasn’t chronicled on television for understandable reasons related to Kylie being a minor who deserved privacy.

But, um, here’s some hard evidence of their relationship that’s just randomly floating around the internet:

CODY SIMPSON: 2011

Before he and Gigi Hadid got together, Cody Simpson was in a “relationship” with Kylie. Again, the level of public interest in her just wasn’t as intense back then (it was simply reported that they were a “couple”), so there’s not that much info on the interwebz about their fling. Cody did open up about their breakup on Hello Ross, saying, “The whole K-O-D-Y thing didn’t work for me.” IDK, feels unnecessarily shady to me.

JADEN SMITH: 2013

Wondering how Kylie met her ex-BFF Jordyn Woods? Through Jaden Smith! Kylie and Jaden low-key dated in 2013 (but never confirmed their status), and rumor has it that he was one of the reasons Kylie and Tyga broke up in 2015. “Kylie and Jaden have been hanging out lately and it made Tyga suspicious,” a source told E! News. “He thought something might be going on. So that was one issue.”

Kylie and Jaden have remained friends through the years, but, well, the Smiths made their feelings known during the whole Tristan Thompson/Jordyn Woods cheating scandal...so who knows what the state of their friendship is currently. (FWIW, Jaden doesn’t follow Kylie on Instagram—but she follows him.)

LIL TWIST: 2013

TMZ reported that Kylie and Lil Twist were dating in 2013, claiming that they went on a date just a week after she went to the movies with Jaden. They were SUPER flirty on Twitter for a while, so go ahead and read into it:

While this relationship was brief, Kylie and Lil Twist were still friendly in 2014. Here they are cozying up on Kendall’s IG:

TYGA: 2014 to 2016 (ISH)

Ugh, where to even start? Kylie and Tyga met at Kendall Jenner’s Sweet Sixteen Party in 2011, where he performed:

They started hanging out more seriously in 2014, but Tyga denied rumors they were dating:

There was a ton of controversy largely due to Kylie’s age (she was a minor at the time), and they got a lot of side-eye, including from Kanye West’s ex Amber Rose, who told the Breakfast Club, “[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.”

The couple finally went Instagram official after Kylie turned 18 and spent the next few years breaking up and making up before calling it quits for good in April 2017. Tyga has remained petty ever since, even taking credit for Kylie’s Lip Kits.

PARTYNEXTDOOR: 2016

Rumors about Kylie and PartyNextDoor took off when she was seen making out with him in his video for “Come and See Me”:

Their “relationship” was, erm, obviously an attempt to make Tyga jealous, and Kylie played it off in an interview with Complex, saying, “Me and Party have a cool relationship. I think he’s so talented and I love his music. 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 to 2023

Kylie and her ex-boyfriend, Travis Scott, started dating in April 2017, and things heated up *fast*. Head here for a full timeline, but basically, they got together, she got pregnant, they were together, broke up, got back together, had another baby, and now are off again.

According to a what a source told People, their present breakup is because of lifestyle differences. “Kylie is very focused on her kids and her business,” the insider said. “She is not a big partier. Travis is the opposite. He likes to party. They definitely have different focuses. They always did.”

But, considering their history, this miiight not be the end end, said the source. “They have split several times in the past and this is probably not the end of their relationship.” Guess we shall see!

TIMOTHÉE CHALAMET: present (maybe)

Ohhhh, yeah. I'll give you a moment to collect yourself. Basically, this rumor (emphasis there!!) came to light by none other than DeuxMoi when a tipster wrote, "Anon pls!! Multiple sources have told me that Timmy C has a new girl...Kylie Jenner" with a few coffin emojis because it's the only appropriate addition. Someone else then spoke up with, "I heard they are both going to be at Coachella." Then! Another person cosigned this, saying, "I can 100% confirm that." FWIW, DeuxMoi diiid put her "Read With Caution" gif, which basically means take this intel with the largest grain of salt—aka not a damn thing here is confirmed.

But! If you're like me and wanna speculate even deeper, just read this line from a Page Six story about Kendall Jenner and Bad Bunny: "Jenner and Bad Bunny enjoyed a dinner alongside other A-Listers – including her sister, Kylie Jenner and Timothée Chalamet, Zack Bia and Russell Westbrook." Welp!!!!

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