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Kylie Jenner’s Dating History – A Complete List of Boyfriends

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Kylie Jenner has been “married to the Met” before, but who has she really had plans on marrying throughout the years?

Was her long-standing romance with Tyga actually the real-deal, before her on-and-off relationship with Travis Scott? Or maybe Timothée Chalamet is her one true soulmate? 

Although the self-made-billionaire is in the limelight, she’s always managed to keep her love affairs private. Besides, she hid her pregnancy with Travis Scott for an entire nine months. 

To find out what other skeletons she has hiding in her closet, we dug deep to uncover Kylie’s past relationships – including ex-boyfriends and former flames that never made it to our social timelines.

Check out Kylie Jenner’s dating history below… 

Ex: Ramsey IV

Who is He? Singer/songwriter & actor
Dated In: 2008 -2011

Kylie’s love life began at just 12 years-old when she reportedly met her first boyfriend, Ramsey IV. She embarked on a three-year relationship with the singer before breaking up with him.

Although this puppy love romance has never been confirmed, there were numerous pictures of the duo together that sparked interest. 

Ex: Cody Simpson

Who is He? Singer 
Dated In: 2011

Kylie and teen-throb Cody enjoyed a short-lived romance together in 2011, but kept the relationship fairly private.

Although he went on to date Miley Cyrus and Gigi Hadid, not much has been said about Cody’s brief link to Kylie Jenner, except these cute photos that went public in 2014.

Cody also recently mentioned that Kylie was his “very first girlfriend” in an interview with NOVA FM’s Fitzy and Wippa.

Rumored Ex: Jaden Smith

Who is He? Rapper & Actor
Dated In: 2013

Growing up in the same circle, Kylie and Jaden were really good friends before they apparently started having romantic feelings for each other.

While they never confirmed their loving relationship, they were spotted going to the movies hand-in-hand, attending red carpet events together, and erm, kissing

Kylie once dubbed him her “best guy friend”, but that didn’t stop the hook-up rumors from swirling.

As they grew older, it seems the pair grew apart and embarked on different relationships. Jaden then went on to publicly date Amandla Stenberg and Kylie laid eyes on another rapper…

Rumored Ex: Lil Twist

Who is He? Rapper
Dated In: 2013 & 2014

After sharing flirty tweets which included the words, “I love you”, fans were convinced that Kylie and Lil Twist were seeing each other.

They were even spotted hanging out in West Hollywood, just days after jewelry shopping with Jaden Smith.

That said, there was no real confirmation that these two were more than just flirty friends. 

After headlines ran rampant about the apparent affair, Kylie tweeted, “Media always making it seem like I’m dating everyone I’m seen with.. Makes no sense to me. Don’t listen to everything u see, people.”

Rumored Ex: Justin Bieber

Who is He? Singer
Dated In: 2014

Justin has come to Kylie’s defense plenty of times in the past and it’s no secret that the pair have had an extremely close relationship. Selena and Justin even split-up over his closeness with the reality TV star. 

When talking about Justin during an interview for ELLE magazine, Kylie said, “I’m so close to him because I feel like he’s been through exactly what I’ve been through in a completely different way but very similar.” 

She continued, “So he’s just…he just… gets me, and every time I see him he always sits me down and is like, ‘Are you OK? You’re amazing. You can get through this, just stay true to yourself.’ He helps me a lot.” 

However, that closeness was confused with a physical relationship. We can confirm, however, that these popular celebs were just good friends. 

Rumored Ex: Miles Richie

Who is He? Musician
Dated In: 2014

Yet another dude making it to Kylie’s dating timeline is Miles Richie. In 2014, Lionel Richie’s famous son was spotted dropping Kylie off at her hair appointment. What’s more, a video obtained by TMZ showed the fashionista tattooing her own initials on his hand at a Hollywood recording studio.

Despite these occasions, the pair never confirmed or denied a fling. 

Ex: Tyga

Who is He? Rapper
Dated In: 2014 – 2017

Kylie’s first public relationship was with Tyga, but it faced a lot of controversy, as the makeup mogul was just 14 when they first met – after he was booked for Kendall’s 16th birthday party. 

The couple didn’t make it Instagram-official until Kylie turned 18, and their relationship was widely publicized and documented on Keeping up with the Kardashians.

Their love story, however, received a lot of backlash as Tyga’s ex, Blac Chyna (whom they share a son together) claimed that Kylie was the cause of the end of their engagement. 

Although they had their struggles, Kylie and Tyga seemed to be in it for the long-run after she revealed a promise ring in 2016, proving that they had plans to get married one day.

That came to a permanent end, though, when the couple ended things (on “good terms”) in 2017. Discussing her split on Life of Kylie, the fashionista said,

“There was absolutely not one thing wrong with me and T,” she says. “Him and I will always, always have a bond. There was no crazy fight. We just decided, well, I decided that I’m really young. I don’t want to look back five years from now and feel like he took something from me when he’s really not that type of person.” 

Rumored Ex: A$AP Rocky

Who is He? Rapper
Dated In: 2015

Another rapper among Kylie Jenner’s dating history is A$AP Rocky. Indeed, Kylie apparently dated Rihanna’s boyfriend and baby daddy a few years back. Kylie was reportedly linked to the rapper in 2015, when fans started questioning their romantic relationship. 

However, eyes were on the wrong Jenner sister. A$AP was actually dating Kendall for a while between 2016 and 2017, but they parted ways due to their busy schedules. 

Rumored Ex: Stitches

Who is He? Rapper
Dated In: 2015

In 2015, rapper Stitches claimed that he and Kylie got intimate while she was still dating Tyga. He shocked the world by saying they did drugs together and then got physical, but once Kylie blocked his number, the rapper took revenge by creating a diss track called, Kyga She’s a Liar. 

After the song was released, Tyga had his team call Stitches’ manager to remove the track, but Stitches wouldn’t back down and they were on the brink of a very violent feud.

Rumored Ex: InkMonstarr

Who is He? Rapper
Dated In: 2015

On the same diss track aimed towards her then-boyfriend Tyga, another rapper that claimed he got with Kylie was InkMonstarr.

After the release of the song, he took to Instagram to leak DMs that the two apparently shared, with a picture of them that was a few days old. 

Rumored Ex: PARTYNEXTDOOR

Who is He? Singer
Dated In: 2016

After appearing in the rapper’s music video for his track Come and See Me, fans were led to believe that Kylie and PARTYNEXTDOOR were an item; especially as they were seen kissing.

Even a video captured by TMZ sorta confirmed the romance.

But in 2016, during her interview with Complex magazine, Kylie confirmed that they were never ‘boyfriend and girlfriend’, but were simply having fun.

She did confirm that she thought PARTYNEXTDOOR was a really cool guy and was a fan of his artistry, “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.”

Rumored Ex: Tim Chung

Who is He? Kylie’s bodyguard
Dated In: 2018

Throughout her on-and-off relationship with Travis Scott (more on him below), crazy rumors started flying in 2018 that Kylie’s bodyguard was actually the father of her baby Stormi – but of course, they were false. To stop all the drama, Kylie’s private bodyguard had to issue a public statement. 

Here is what he said: “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.”

Rumored Ex: Drake

Who is He? Rapper
Dated In: 2019

Amid her break with Travis Scott, Kylie was spotted hanging out with Drake at his 33rd birthday party. 

Rumors circulated that they were casually involved with each other, and according to US Weekly, had “mutual feelings” for one another.

The source revealed that “they have known each other and been friends for a very long time, and there has always been a spark there, but their situation is complicated and so is Kylie’s with Travis.”

Eventually, it seemed Kylie wasn’t interested in anything serious with the hitmaker. Later, Drake’s lyrics from a leaked mixtape featured him calling Kylie a “side piece”, which he later apologized for: “Last thing I’d want to do is wake up and have any friends of mine feeling disrespected so I just had to say that to start off the day,” he said.

Rumored Ex: Fai Khadra

Who is He? Model
Dated In: 2020

Fai is widely known as Kendall’s BFF and Jordyn Woods’ ex (awks). He’s often featured in photos with the Jenners and occasionally makes an appearance on their reality TV show. 

But in 2020, again, during her break with Travis, there was a lot of speculation that the famous Palestinian model was dating the youngest Jenner sister.

Although they posted a lot of pictures together, neither party commented on the nature of their relationship. 

Ex: Travis Scott

Who is He? Rapper
Dated In: 2017 – 2023

Kylie and Travis Scott started dating in 2017 when they met at Coachella. Shortly after, Kylie decided to go on tour with the rapper and just five months after meeting, Kylie fell pregnant with their firstborn, Stormi. 

A few years down the line and the couple were already involved in cheating rumors. Apparently, Kylie had found flirty DMs on Travis’ phone, which led to him deactivating his account for a while. In 2020, the duo went their separate ways, but remained good friends and co-parented their daughter. 

It’s unclear if the pair got back together in 2020, as Mason (Kylie’s nephew) leaked to fans that, “no, Kylie and Travis are not back together” and other sources claimed their relationship was “shaky”. 

Fast-forward to 2021, and the celebrity couple seemed stronger than ever when Kylie and Stormi flew to New York to attend the Parsons Benefit where Travis was being honored and walked the red carpet as a family. During his speech, Travis thanked his girls by saying, “Stormi, I love you and wifey, I love you.”

In that same year, Kylie announced that she was expecting a second child, who was born in February 2022. 

Although they seemed like a happy family of four, Kylie and Travis split up for good at the start of 2023. According to People Kylie and Travis broke up because she “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.”

Rumored Boyfriend: Timothée Chalamet

Who is He? Actor
Dated In: 2023

Here’s someone on Kylie’s dating list we didn’t see coming! That’s right, Oscar-nominated actor Timothée Chalamet is reportedly dating Kylie Jenner. This surprising newsflash came about after DeuxMoi announced, “Anon pls!! Multiple sources have told me that Timmy C has a new girl…Kylie Jenner.”

A TikTok of the duo embracing went viral, and Kylie’s car was then spotted outside Timothée’s house, leading fans to believe this Hollywood fling was very much real.

A source told People, however, that “It’s not serious. Kylie is having fun. After years of back and forth with Travis [Scott], she just wants to date without any pressure.”

After Kylie’s rocky path to love, we hope that she commits to Timothée for the long-run – they would definitely be the Hollywood couple of the century! Do you agree?

Let us know which of Kylie Jenner’s boyfriends you feel she was best suited to throughout her relationship history… 

This article was originally published in May 2022.



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