Kylie Jenner may joke that she’s “married to the Met,” but when it comes to her actual love life, things have been a lot more complicated—and way more interesting.
From her headline-making romance with Tyga and years-long on-and-off relationship with Travis Scott, to her surprisingly low-key but seemingly solid romance with Timothée Chalamet, Kylie has had her fair share of famous relationships. These days, the beauty mogul and mom-of-two can’t seem to keep their hands off each other, serving up PDA at award shows, NFL games, and red carpets while fans continue to obsess over the unexpected pairing.
But before Timmy entered the chat, there were plenty of rumored flings, ex-boyfriends, and relationships that flew under the radar. We took a deep dive into Kylie Jenner’s complete dating history—from her earliest romances and ex-boyfriends to the man who might just be her endgame.
Who is Kylie Jenner dating now?
Kylie Jenner is currently dating actor Timothée Chalamet. The pair first sparked romance rumors in 2023 and have since become one of Hollywood’s most unexpected power couples, regularly stepping out together and packing on the PDA at major events. More on that below!
A List of Kylie Jenner’s Boyfriends Over the Years
FYI: Other than her official romances, this list also contains guys that Kylie was *rumored* to be dating.
Jump to:
- Ramsey IV
- Cody Simpson
- Jaden Smith
- Lil Twist
- Justin Bieber
- Miles Richie
- Tyga
- A$AP Rocky
- Stitches
- InkMonstarr
- PARTYNEXTDOOR
- Tim Chung
- Drake
- Fai Khadra
- Travis Scott
- Timothée Chalamet
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 heartthrob Cody Simpson 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.
But in 2022, all was confirmed when Cody made it official 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.
SEE ALSO:
Kylie Jenner’s Transformation Over the Years
Kylie once dubbed him her “best guy friend”, but that didn’t stop the hook-up rumors from swirling. As they grew up, 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
It’s no secret that Justin and Kylie have had an extremely close relationship over the years. I mean, Justin and Selena Gomez even reportedly split-up over his closeness with the reality TV star.
When talking about Justin during an interview with ELLE, 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.”
So yeah, their closeness was basically confused with romance. I think it’s obvious these two major stars were just good friends. I mean, Kylie is even BFFs with Justin’s wife!
Rumored Ex: Miles Richie
Who is He? Musician
Dated In: 2014
Yet another guy making his mark on 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.
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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.
It all came to an end, though, when the couple ended things (on “good terms”) in 2017. Discussing her split on Life of Kylie, the beauty star 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 listed in Kylie’s dating history is A$AP Rocky. Yep, Kylie apparently dated Rihanna’s man and baby daddy a few years back. She was reportedly linked to the rapper in 2015, when fans started questioning their romantic relationship.
However, eyes were on the wrong Jenner sister. A$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 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.
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But in 2016, during her interview with Complex, 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 where he wrote:
“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.”
SEE ALSO:
Drake’s Dating History – Girlfriends List
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 he and Kylie 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 attended 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.
CHECK OUT:
The Kardashian & Jenner Family Tree
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.”
Boyfriend: Timothée Chalamet
Who is He? Actor
Dated In: 2023 – now
Here’s someone on Kylie’s dating list we definitely didn’t see coming! In one of Hollywood’s most unexpected romances, Kylie Jenner and Oscar-nominated actor Timothée Chalamet first sparked dating rumors in 2023 after celebrity gossip account DeuxMoi claimed the pair were seeing each other. Fans were skeptical at first, but after Kylie’s car was spotted outside Timothée’s home and the pair were later photographed kissing and cuddling at Beyoncé’s concert, it became clear the romance was real.
Since then, Kylie and Timothée have gone from secretive dates to one of Hollywood’s hottest couples. They’ve packed on the PDA everywhere from the Golden Globes and Oscars to Coachella, tennis tournaments, and NBA games, with fans regularly spotting them kissing, holding hands, and looking completely smitten.
In 2025, the pair made their official red carpet debut together at the David di Donatello Awards in Rome, marking a major milestone in their relationship. As of 2026, they appear stronger than ever, with Timothée becoming increasingly close to Kylie’s family and she’s been supporting him at major events, proving this unexpected romance may have more staying power than anyone predicted.
From teenage romances and headline-making breakups to becoming a mom of two and finding love in the most unexpected place, Kylie Jenner’s dating history has certainly kept fans invested. While only time will tell where her relationship with Timothée Chalamet leads, the pair seem happier and more loved-up than ever.
Now it’s your turn—of all Kylie Jenner’s relationships over the years, which boyfriend do you think suited her best? And do you think Timothée could be the one she finally goes the distance with?
This list was originally published in May 2022 and was last reviewed and refreshed in 2026 to include Kylie’s more recent romances. Co-written with Angela Stephanou.
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