A Glimpse into Kylie Jenner's Dating History
From Tyga to Timmy.
by OLIVIA BOYER ★ OCTOBER 16, 2023
While being in the limelight has its perks, it also means people are constantly digging into your personal business. Unfortunately for Kylie Jenner, the most private of the Kardashian clan, fans constantly speculate about what is going on in her love life. Kylie Jenner’s boyfriends have been the talk of the town since she was the age of 14. Here is an up-to-date list of Kylie’s romantic partners over the years;
2011: Cody Simpson
To start the tangled web of Jenner’s dating history, we need to start at the beginning; Cody Simpson and KJ coupled up when they were both just 14. The pair met at – get this – the Twilight Series Breaking Dawn: Part 1 premiere (could it get more 2011?) and dated until an unconfirmed breakup a few months later.
Ah, young love, so fleeting.
2013: Jaden Smith (Unconfirmed)
In 2013, both Kylie and Jaden called each other their “best friend” and appeared suspiciously close in photos. While neither ever confirmed the relationship, they always seemed to have a vibe, with seemingly romantic Instagram captions.
2015 - 2017: Tyga
While Kylie and Tyga first met sister, Kendall Jenner, at her birthday party in 2011, the pair didn’t make it official until 2015. The couple is commonly known for their drastic age gap of 10 years. Tyga, 24 at the time, didn’t help the rumors by hosting Kylie's 17th birthday party at his home, later insisting they were just friends. Pretty hard to believe if you ask me.
For her 18th birthday, Tyga got her a Ferrari and a tattoo dedicated to her, confirming their relationship. The pair broke up briefly in 2016, only to get back together a few months later. Tyga and Kylie were very on again off again, something that all of us have been through.
In the spring of 2017, Tyga and Kylie broke up again, permanently this time, with Kylie opening up about the split on her reality TV show, Life of Kylie.
2017-2019: Travis Scott
Travis and Kylie are one of the most well-known power couples of our times. The pair will always be connected. They’ve come back to each other multiple times, primarily due to the two children they share.
The couple was first rumored to be together during Coachella of 2017. By September of the same year, Jenner was pregnant with their first child, Stormi. The baby wasn’t announced until her birth in February. They stayed together for two years before breaking up in the fall of 2019.
2019: Drake (unconfirmed)
Drake and Kylie were spotted together multiple times during her time away from Travis Scott. Though unconfirmed, the pair was said to be flirting and close, especially since Drake and Kylie had been friends for years.
2021-2023: Travis Scott, again
The power couple reunited in 2021 and announced they were expecting their second child. Their baby boy, Aire, was born just a day after Stormi’s 4th birthday. Travis Scott and Jenner broke up for a second time in early 2023. It was heartbreaking; everyone and their moms were broken up about the split.
September 2023: Timotheé Chalamet enters the scene
This iconic duo has been spending time together since April of this year, a few months after her split with Scott. Before that, fans have been speculating about the two spending time together, especially given her split with Travis Scott.
The couple was finally confirmed just a few weeks ago at Beyoncé's birthday performance of her Renaissance tour, making out in the VIP booth.
Since then, they have been spotted together at several events, and Timothee is her phone background. Hopefully, this love lasts, or if it doesn’t, I’m sure the single ladies would love to have Timmy back.