Kylie Jenner has been in the spotlight since she was literally nine years old. That is a lot of time for people to speculate about her personal life. Honestly, it’s kinda wild how many "confirmed" boyfriends turn out to be just friends or a one-off hanging out session at a party. When you look at the question of kylie jenner dated who, the list is actually shorter than the tabloids make it seem, though the names on it are massive.
The biggest shocker lately? Timothée Chalamet. People thought it was a PR stunt. They said it wouldn't last three months. Well, here we are in 2026, and they are still going strong. He’s even thanking her in award speeches now.
But before the Oscar-nominated actors and the matching leather outfits at the Marty Supreme premiere, there was a decade of high-profile rappers and teenage flings. Let’s get into the reality of her dating history without the fluff.
The Early Years: Cody Simpson and Jaden Smith
Back in 2011, Kylie was just a kid on a reality show. She met Australian singer Cody Simpson at the Breaking Dawn: Part 1 premiere. They were 14. It was cute, flirty, and very much a middle-school vibe. They dated for a few months before fizzling out. Cody eventually moved on to Gigi Hadid and Miley Cyrus, but Kylie was just getting started.
Then came Jaden Smith in 2013. This one is interesting because they’ve never really stopped being close. They were "best friends" who were spotted making out at Kim and Kanye’s wedding in 2014. It was that classic "are they or aren't they" situation. Even though they haven't been romantic in years, Jaden is still a staple in the Kardashian-Jenner inner circle.
The Tyga Era: A Relationship That Defined an Era
You can’t talk about kylie jenner dated who without spending a lot of time on Tyga. This was messy. They met when she was 14 at Kendall’s birthday party, but things didn't get "official" until she turned 18 in 2015.
The optics weren't great. He was 25; she was still a teenager. He gave her a Ferrari for her 18th birthday. He got a tattoo of her name. For three years, they were the "It" couple of Calabasas, constantly breaking up and getting back together.
- 2014: Rumors start while she’s still 17.
- 2015: Relationship confirmed at her 18th birthday bash.
- 2016: A brief split, then a reconciliation.
- April 2017: The final breakup.
Kylie later said on Life of Kylie that there wasn't one big fight. She just realized she was too young to be in something so serious that felt like it was "taking something" from her. It was a clean break, mostly.
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Travis Scott: The Father of Her Children
Literally the same month she split with Tyga, Kylie was spotted at Coachella with Travis Scott. Things moved fast. Like, really fast. Within weeks, they were inseparable. By September 2017, the internet was melting down because she had disappeared from the public eye.
She was pregnant.
Stormi Webster was born in February 2018. For the next few years, Kylie and Travis were the ultimate power couple. They did the Playboy shoots. They did the Grammys. They broke up in 2019, but then the pandemic hit, and they quarantined together.
By 2021, they were back on and expecting baby number two. Aire Webster arrived in early 2022. But by January 2023, the "on-again, off-again" cycle finally broke for good. They’re reportedly great co-parents now, but the romantic spark seems to have stayed in the past.
The Drake and Fai Khadra Rumors
After the first Travis split, everyone wanted to know who Kylie was seeing. There were heavy rumors about Drake in late 2019. They were "spending time together," but sources close to the family insisted they were just longtime friends. Drake has been around the Kardashians forever, so it’s hard to tell where the friendship ended and the flirting began.
Then there’s Fai Khadra. He’s Kendall’s best friend, but he’s often seen as Kylie’s "plus one" to weddings and vacations. Despite the steamy Instagram photos, these two have never confirmed anything beyond a very close-knit friendship.
Timothée Chalamet: The Unexpected Endgame?
When the news broke in early 2023 that Kylie was dating the Dune star, nobody believed it. It felt like two different universes colliding. But then came the Beyoncé concert in September 2023, where they were caught on camera kissing in the VIP section.
Fast forward to January 2026. This isn't just a fling anymore.
- Red Carpet Official: They finally made their debut as a couple at the David Di Donatello Awards in May 2025.
- Moving In: Reports from early 2026 suggest they’ve been living together in Los Angeles for over a year.
- Public Declarations: At the 2026 Critics Choice Awards, Timothée thanked Kylie as his "partner of three years" during his Best Actor speech.
It’s a different vibe for Kylie. It’s quieter. More "low-key luxury" than "rapper girlfriend." He’s met her kids, and according to insiders, they behave like they're "basically married."
What to Keep in Mind
If you're following the kylie jenner dated who timeline, remember that she’s incredibly private for someone so famous. She often hides her relationships for months before confirming them. If you see a rumor about her and a new guy tomorrow, check the following:
- The "Car in the Driveway" Test: TMZ usually gets photos of her Range Rover at a guy's house before any official statement.
- The Family Approval: If they aren't at a Kardashian Christmas party, it probably isn't serious.
- The Award Show Seat: Since 2024, she’s been Timothée’s constant companion at ceremonies, often skipping the red carpet but sitting right next to him inside.
To keep up with the latest confirmed updates, watch The Kardashians on Hulu, but take the "single" narrative with a grain of salt—she usually films months in advance. Check recent paparazzi galleries from major LA restaurants like Sushi Park or Giorgio Baldi, as those are her go-to spots for "secret" dates.