Kylie Jenner has been in a truly sweet relationship with actor Timothée Chalamet, but—much like the rest of us—she had to metaphorically swipe left on a buncha dudes to find him. (I mean, no offense to anyone on this list. I’m sure you’re all great!)
And if you’ve been keeping up with the Kardashians, you already know the Kylie Cosmetics founder dated Tyga before she and Travis Scott fell in love and welcomed their adorable kids Stormi and Aire to the world—but those are just two of the celebs' 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? Whelp, 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 the seventh grade?! Like, they didn’t even have good selfie-taking skills yet lol:
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.
That! Said!!! Here’s some hard evidence of their romance that’s still randomly floating around the internet for some reason:
Cody Simpson: 2011
![kylie jenner cody simpson](https://hips.hearstapps.com/hmg-prod/images/gettyimages-135168232-1-1565104830.jpg?resize=980:* "Teen Sensations Invade Buca di Beppo For Popstar! Magazine's "12 In '12"")
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” at the time), so there’s not that much info on the interwebz about their fling. Cody did, however, open up about their breakup on Hello Ross, and mused, “The whole K-O-D-Y thing didn’t work for me.” IDK, feels unnecessarily shady to me.
Well! Then!!!
Jaden Smith: 2013
Wondering how Kylie met her on-again BFF Jordyn Woods? Through Jaden Smith! Kylie and Jaden low-key dated back in 2013 (but never confirmed their status), and rumor has it 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 at the time. “He thought something might be going on. So that was one issue.”
Btw, 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, neither Jaden nor Kylie follow each other on Instagram. 👀)
Lil Twist: 2013
TMZ reported that Kylie and rapper Lil Twist were dating in 2013 and claimed they went on a date just a week after she went to the movies with Jaden. And, I mean, they were SUPER flirty on Twitter for a while, so go ahead and read into it:
While this 'ship 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 then began hanging out more seriously in 2014, but Tyga denied rumors they were dating:
There was a ton of controversy between the celebs largely due to Kylie’s age (she was a minor at the time), and they kinda 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. Btw, Tyga has remained petty ever since, even taking credit for Kylie’s Lip Kits. ¯\_(ツ)_/¯
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, began 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 what a source told People, their final breakup was ultimately caused by lifestyle differences: “Kylie is very focused on her kids and her business. She is not a big partier. Travis is the opposite. He likes to party. They definitely have different focuses. They always did.”
Honestly? Fair!
Timothée Chalamet: April 2023 to Right TF Now!
Ohhhh, yeah. I'll give you a moment to collect yourself. Basically, this 'ship came to light by none other than DeuxMoi after 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 added, “I heard they are both going to be at Coachella.” But wait! There's more... Another person then cosigned all this and noted, “I can 100% confirm that.”
Just a few weeks later, Entertainment Tonight finally gave us an answer on the rumored romance, which was *drumroll, pls* that these two were, in fact, officially dating. According to a source, Kylie and Timmy were “keeping things casual at this point.” More specifically, the 'ship was “not serious,” but “Kylie is enjoying hanging out with Timothée and seeing where it goes.” Plus, apparently, “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.”
And if that 🍵 wasn't enough, the celebs seemingly hard-launched their 'ship at the happiest place on Earth: Beyoncé's Renaissance World Tour.
Anyway! In the event you're in the mood to obsess over their entire 'ship, which has since gotten much more serious (like, these two legit exchanged “I love you's” at the freakin' Golden Globes!!!!!), head right on over this way:
