Since starting their relationship in April of this year, Kendall Jenner and Jacob Elordi have been the latest IT couple. However, before finding each other, the model had her fair share of love fails in several high-profile relationships.
It comes as no surprise that the latest episode of “The Kardashians” saw Jenner lament her dating past during a candid discussion with long-time friend Cara Delevingne. While addressing rumors of being a lesbian, Jenner joked that she’d prefer to date women because “men suck.”
Here is a trip down memory lane of some of Jenner’s famous exes and what went down between them.
Harry Styles
Kendall Jenner and Harry Styles were first rumored to be dating back in November 2013, but they described themselves as just friends at the time. However, their connection appeared to continue on and off for several years, including a New Year’s trip to St. Barts in 2016.
Jenner’s sister Khloé Kardashian suggested they were dating but wasn’t sure whether they had officially defined their relationship. In 2019, the pair reunited on “The Late Late Show” and played “Fill Your Guts or Spill Your Guts.”
Jenner asked Styles which songs on his previous album were about her, but he chose to eat cod sperm rather than answer, as reported by E! News.
Nick Jonas
Jenner was linked to Nick Jonas in 2015 through her friendship with Gigi Hadid, who was dating Jonas’ brother Joe at the time.
The pair reportedly began texting with a flirty connection, but Nick denied that they were dating. He said Jenner and Hadid were friends and that they sometimes spent time together because of their shared social circle. They were never confirmed to be romantically involved.
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- Elordi and Jenner took their romance to the actor’s hometown as they got closer
- Kendall Jenner also took Elordi to see “sad and lonely” Caitlyn.
Jordan Clarkson
The New York Knicks player seemed to be Jenner’s first introduction to dating athletes.
The “KUWTK” alum was linked to basketball player Jordan Clarkson in 2016 after they were spotted together.
According to Hollywood Life, they spent time together throughout the year, and an eyewitness described them as affectionate at a 2016 American Music Awards after-party. They were also seen together at Coachella.
However, their connection appeared to remain casual, and the pair reportedly went their separate ways later that year.
A$AP Rocky
Before his family life with Rihanna, A$AP Rocky and Jenner were reportedly romantically involved.
The pair sparked romance rumors after attending Kanye West’s Yeezy fashion show together in August 2016. They were later spotted together at the 2017 Met Gala.
Although they were romantically linked for more than a year, they never made their relationship official. By September 2017, reports suggested they were not seeing each other often and that their busy schedules made it hard to maintain their connection.
Blake Griffin
Jenner was reportedly linked to basketball player Blake Griffin in August 2017. Their relationship appeared to become more serious over the following months, and Jenner was seen attending his games.
In March 2018, she said she was happy and had someone who treated her well in an interview with Vogue, without directly confirming Griffin was the person she meant.
Their relationship reportedly ended after Griffin moved from Los Angeles to Detroit, making it more difficult for them to spend time together.
Ben Simmons
Shortly after, Jenner began dating basketball player Ben Simmons in 2018. She acknowledged their relationship during a February 2019 appearance on “The Ellen DeGeneres Show,” saying they had been dating “for a bit.”
That May, she said marriage was a possibility in the future. However, the relationship reportedly went on a break later that month. The pair’s romance was on and off, with reports of reconnecting before eventually separating.
Devin Booker
Another high-profile relationship of the model’s was with Devin Booker. Jenner and Booker were first linked in 2020 after taking a road trip through Arizona.
Their relationship became more public in 2021 when Jenner shared a Valentine’s Day post featuring the basketball player. They continued dating into 2022, briefly split, and later reconciled before separating again that October.
Jenner was subsequently linked to Booker again in 2024 and early 2025, sparking speculation about another reunion. However, in January 2026, she said she was single and had been for a while.
Bad Bunny
Jenner was linked to Bad Bunny in early 2023 when they were seen leaving a restaurant together. Their relationship became more public in the months that followed, and they appeared together at Gucci’s Milan Fashion Week show.
They reportedly split in December 2023 but were later seen spending time together again. In May 2024, reports indicated they had reconciled and were prioritizing time together after a hotel sighting.
By September, however, they had reportedly separated again, although they remained friendly.
Jacob Elordi
After a string of fails and being single for a while, Jenner surfaced with Elordi as her love interest in April 2026, when it was reported they were getting to know each other.
The pair were then seen together in Hawaii and at Paris Fashion Week in September.
Their reported romance has attracted attention, but Jenner has generally kept her personal life private as she is yet to comment on her connection with the “Euphoria” actor.