Here's An Absurdly Detailed List of Every Guy Kylie Jenner Has Ever Dated
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Even as one of the most-followed people on Instagram, Kylie Jenner has always kept the details of her love life mostly private. Apart from the breakups, babies, and bloody feuds with boyfriends' exes, that girl has kept her relationships as secret as her pregnancy – and judging by the suspicious lack of information available, those non-disclosure agreements are airtight.
That being said, there's some pretty heavy evidence that Kylie has had multiple relationships that most fans probably didn't even know about (read: Cody Simpson). To save you valuable hours of Instagram stalking, I dug deep into all of Kylie's serious boyfriends, past flings, and random bros you'll never believe she once dated.
Keep on reading for a full breakdown of every boyfriend Kylie Jenner has ever had.
Who is Kylie Jenner dating right now?
Kylie Jenner and Travis Scott
Kylie began her relationship with Travis Scott (his real name is Jacques Bermon Webster II) in April of 2017. The two met when Travis performed at Coachella on the California leg of his 2017 tour. They immediately noticed a spark, so Kylie picked up everything and hit the road, traveling with Travis on his tour.
"Coachella was one of the stops on his tour," Kylie dished in an interview with GQ. "So he said, 'I'm going back on tour—what do we want to do about this?' Because we obviously liked each other. And I was like, 'I guess I'm going with you.' "
One month later, Kylie was pregnant with their first child, Stormi Webster, who was born on February 1, 2018 after a top-secret pregnancy.
In the past, both engagement and cheating rumors have made their way to the press. In 2019, TMZ reported that Kylie found some "overly friendly" DMs to girls on Travis' Instagram. Right after news broke, Travis temporarily deactivated his Instagram account and cancelled a show on his Astroworld tour claiming he was ill. Travis has denied the cheating claims.
In October of 2019, the two finally split, but Kylie told fans they're "on great terms." The two successfully co-parented for a few months, before sort of getting back together in March of 2020. A source told People: "Things are great with Kylie and Travis. They are very happy. Kylie still isn’t labeling their relationship. It seems they aren’t seeing other people, though."
Shortly after this, Kylie's nephew Mason Disick told fans "no, Kylie and Travis are not back together" and in September 2020, reports surfaced that their relationship is "so shaky." A source told Us Weekly that "they are so on and off and it changes almost month to month."
Though many fans thought Kylie was dating family friend Fai Khadra during the "off" times (I doubt it, but ok), Stormi's parents have made it clear that they're back on. On June 15 2021, both Kylie and Stormi flew out to NYC to attend the Parsons Benefit where Travis was being honored and walked the red carpet as a family. E! reports that in his speech, Travis thanked both his daughter and his gf, saying: "Stormi, I love you and wifey, I love you."
Now, major outlets like People and E! (home of Keeping Up With the Kardashians) have confirmed that the couple is expecting their second child together. Mom and Dad haven't yet commented on the news themselves, but, trust me, I'm on the lookout. 👀
Who has Kylie Jenner dated in the past?
Kylie Jenner and Fai Khadra (maybe?)
Buckle up, y'all, cause this alleged relationship is MESSY. In 2019, rumors were positively *swirling* that model Fai Khadra was dating Kendall Jenner. The two rocked a couples' costume last Halloween and Kendall has even joked about "starting a family" with him, but she has confirmed they are just friends, saying "we don't date."
Two years prior, he was ALSO spotted holding hands with Jordyn Woods, persona non grata #1 of the entire Kardashian/Jenner fam. In 2020, Fai started inexplicably appearing on Kylie's Instagram and fans are absolutely convinced they dated – at least for a minute.
It all started in June 2020, when Kylie started posting sexy lingerie pics clutching a mysterious man-shoulder. 👀👀👀
Clearly, ya girl was trying to send a message. A week later, the makeup mogul went on a family vacation to Utah – cue Fai. The man got a grid post on Kylie's IG (ya, it's looking serious) and a feature in this half-naked carousel.
In August 2020, Kylie somehow found her way around the European travel ban (???) and went on a getaway to Paris, France. Guess who came along for the ride. YUP, Fai. Kylie posted photo evidence on her Instagram Stories AND on the grid (swipe for said evidence).
All of this is majorly important, because Kylie almost never posts photos of people outside of her immediate family/best friend Stassie Karanikolaou to her IG grid (which is fair, considering that kind of exposure is literally worth millions). So now 99% of the internet thinks the two were an item and Kylie has neither confirmed nor denied.
She has, however, posted a birthday shout out to Fai in the form of a whole eight-photo Instagram Story.
Though all this evidence has people thinking they're a thing, I personally don't believe it. Fai has been a Kardashian/Jenner family bestie for years and I'm guessing Kylie's posts are just bff energy. Y'all are gonna have to decide this one for yourself, though.
Kylie Jenner and Tyga
Kylie's first serious relationship was with rapper Tyga (real name: Micheal Ray Stevenson). Their three-year romance included liberal helpings of drama: public feuds with Tyga's baby mama (who later had a baby with Kylie's brother, Rob Kardashian), continuous pregnancy rumors, and multiple messy public breakups.
The former couple first met in November of 2011 at Kendall Jenner's 16th birthday party, when Kylie was 14 years old and Tyga was 21. Years later (July 2014), Tyga makes his first appearance on Kylie's Instagram and that August, celebrates Kylie's 17th birthday with her. Days later, the rapper calls off his engagement to his girlfriend of two years and the mother of his son, Blac Chyna. (The result is about two years worth of shade, drama, and screenshot sharing from Blac Chyna and her crew.)
In October 2014, the two become Instagram official with a couples Halloween costume. The two publically dated from here on out, but claimed they were "just friends" until Kylie turned 18 (Tyga bought her a $320k Ferrari for her bday).
In September of 2016, Kylie unveiled a massive promise ring, revealing that the two plan to one day get married.
Unfortunately, that day never came. They dated off and on until April of 2017, confirming their split just weeks before Kylie is seen holding hands with Travis Scott at Coachella.
Kylie Jenner and Jaden Smith
Although they never officially admitted to dating, it's widely believed that Will Smith's son, Jaden was Kylie's first love back in 2013. Jaden actually introduced Kylie to her lifelong best friend (now, ex best friend) Jordyn Woods when they were 13 years old.
During that time, Kylie denied rumors of their relationship, telling Seventeen that Jaden is just a close friend. "I don’t have a boyfriend, but I do really want that boyfriend prom experience," she said.
Later on in the interview, though she did name-drop Jaden, sharing that if she needed a date to prom, she "would want to go with one of my best guy friends, like Jaden [Smith]. I know I’d have fun with him – he makes me laugh and he is a great dancer."
It's unclear how long the two actually dated for, but two years later, Kylie got into a pretty public argument with Jaden's then girlfriend, Amandla Stenberg. After Amandla bashed Kylie for wearing cornrows, Kylie responded "Mad if I don't, Mad if I do.... Go hang with Jaden or something."
It seems that Kylie and Jaden later made up, because they were spotted later that year at a Justin Bieber concert looking friendly.
Kylie Jenner and Cody Simpson
Before Jaden, Kylie briefly dated singer Cody Simpson (the pictures are really cute, FYI). Since their short-lived relationship was pre-Instagram, there's not a ton of info on the couple, though Cody did joke about their breakup on Hello Ross.
Host Ross Mathews brought up Kylie, joking that if the relationship had worked out, Cody would have been a Kardashian, to which he responded: "The whole K-O-D-Y thing didn't work for me." At the time, Cody was actually dating Gigi Hadid.
Kylie Jenner and Ramsey IV
According to MTV, artist Ramsey IV was Kylie's first boyfriend. It's rumored that the two dated from 2008 to 2011, starting their romance when Kylie was 12. If these screenshots are to be trusted, Ramsey confirmed they had been dating "3yrs and counting."
Did Kylie Jenner date her bodyguard?
Although the entire internet speculated that Kylie's Hot Bodyguard™ Tim Chung was actually Stormi's father (*eye roll*), the rumors were completely false. Tim even had to issue a statement, shutting down the rumors.
I am a very private person and would normally never answer to gossip and stories that are so ridiculous that they are laughable. Out of deep respect for Kylie, Travis, their daughter together and their families, I would like to set the record straight and say that my interactions with Kylie and her family have been limited in strictly a professional capacity only. There is no story here and I ask that the media no longer include me in any narrative that is incredibly disrespectful to their family.
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