While the majority of the Kardashians are public figures, Kendall Jenner likes to maintain her love life in the shadows. Jenner established rules for whether or not her partner could appear with her on the reality show despite being in her life.
According to Keeping Up with the Kardashians executive producer Farnaz Farjam in 2021, “Kendall always had this rule — she felt like she had to be with someone for at least a year before she let them be a part of the show because she doesn’t always know what people’s intentions are. So that’s why we kind of kept her personal life out of it, just because she had a rule”.
Kendall Jenner: Ex-boyfriends List | Timeline

Over the years, Kendall Jenner has maintained the secrecy of most of her relationships despite being linked to numerous well-known musicians and athletes. The Keeping Up With the Kardashians star has dated a number of famous guys, including musicians Harry Styles and A$AP Rocky and basketball players Ben Simmons and Devin Booker.
“I think you learn different lessons in every relationship,” In a behind-the-scenes video for her Calvin Klein campaign in February 2020, the model made the statement. “So I think I’ve learned so many different things from so many different relationships”.
She also said, “A lot of the relationships have taught me more about myself, which is the most valuable. And like, what I want from a person or from a relationship.”
So, let’s see who was fortunate enough to be her partner over the years.
1) Harry Styles: 2013 – 2016

- Harry Styles, the One Direction heartthrob, and the model were frequently seen together from 2013 to 2014 and even went skiing together, leading to rumors that they were dating.
- When the two were seen kissing on a yacht in Anguilla in 2015, Khloe Kardashian was rumored to have confirmed their relationship.
- Two years later, when they were spotted dining together in LA, the romance rumors were reignited.
2) Jordan Clarkson: 2016

- Jordan Clarkson, a member of the Cleveland Cavaliers and a teammate of Tristan Thompson, the boyfriend of Khloé Kardashian, was rumored to have dated the reality star.
- When the model and basketball player posted videos of one another at Coachella, rumors about their romance started to circulate.
3) A$AP Rocky: 2016 – 2017

- Following their appearance on a date in Paris in July 2016, Kendall was just speculated to have dated rapper A$AP Rocky.
- However, when Jenner and Rocky were spotted cuddling at the 2017 Met Gala, it was claimed that the couple had become serious.
- Even Kim Kardashian, Kendall’s older sister, posted a funny photo of the rapper groping the model’s behind on Snapchat.
4) Blake Griffin: 2017 – 2018

- Jenner began dating the Detroit Pistons point guard in September 2017. A month later, a source close to the model told PEOPLE that the two had formalized their relationship and were now a “full-on couple.”
- She sat courtside at several of his basketball games and backed him at one of his comedic performances. In March 2018, Jenner said to Vogue, “I’m happy. He’s quite pleasant”. However, later on in the month, they split up.
5) Ben Simmons: 2018 – 2019

- Jenner also reportedly dated Philadelphia player Ben Simmons, according to a November 2018 People story.
- The “818 Tequila” proprietor was spotted at the athletes’ contests. According to Elle, the couple started dating in May 2018 and split up in August 2018.
- However, when Jenner resumed returning to Simmons’ games in November 2018, dating rumors started to circulate once more. Kendal was even spotted sporting his jersey.
6) Devin Booker: 2020 – 2022

- After taking a brief break in July 2022, Devin Booker and Kendall officially called it quits in November 2022, after two years.
- According to a source who spoke to E! News, Jenner previously “wanted space and time apart,” but “they have been in touch since and do care about one another”.
- They last appeared together at a friend’s wedding. Even proof of Kendall and Booker’s relationship came from an Instagram story they shared together.
7) Bad Bunny: 2023 – Present

- At Coachella in April 2023, Kendall was spotted being quite cozy with her rumored new beau Bad Bunny. The supermodel was also seen dancing during the musician’s performance at the event.
- A few weeks later, amid rumors that the couple is “getting serious,” they were seen out on a date and together at a Met Gala after-party.
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