When it comes to celebrity relationships, few supermodels have managed to keep their love lives under wraps as effectively as Kendall Jenner. Unlike some of her sisters, who have been in highly publicized relationships (think Khloé and Tristan, Kim and Kanye, Kylie and Travis, Kourt and Scott), Kendall seems to prefer that her romantic entanglements remain private. This is not to say that she’s never been linked to any of the most eligible bachelors in the world – far from it.
Dating in the Public Eye
When you’re a supermodel, your personal life is always going to attract attention from the media and the public. But Kendall has always been a bit more low-key about her relationships than some of her sisters. This doesn’t mean she’s been completely off the radar, though – far from it. In fact, Kendall has been linked to some of the most talented and attractive men in the world, and her relationships have always been filled with drama and excitement. In this article, we’ll be taking a closer look at Kendall’s 11 most notorious celebrity exes and their dating histories.
1. Harry Styles
One of Kendall’s earliest high-profile relationships was with the dashing Harry Styles, one of the most talented members of the British boy band One Direction. The two were spotted together on several occasions, including a memorable appearance at the 2013 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2016. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
A Relationship that Caught Everyone’s Attention
When Kendall and Harry first started dating, they were still relatively new to the public eye. But their relationship quickly became one of the most talked-about topics in the celebrity world, with fans and media outlets alike obsessed with every detail of their romance. Despite the intense scrutiny, the two remained committed to each other, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2016.
What Went Wrong?
So what went wrong in Kendall and Harry’s relationship? According to sources, the two parted ways due to scheduling conflicts and differing priorities. Harry’s hectic touring schedule made it difficult for the two to spend quality time together, and ultimately, this led to the demise of their relationship. It’s a shame, because the two clearly had a real connection, and fans had been rooting for them from the very beginning.
2. A$AP Rocky
After her breakup with Harry Styles, Kendall was spotted with the charismatic rapper A$AP Rocky, who was known for his androgynous style and infectious charm. The two were seen together at various events, including a memorable appearance at the 2017 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2018. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Made Their Relationship Special?
One of the things that made Kendall and A$AP Rocky’s relationship so special was their shared sense of humor and playfulness. The two were known for their fun and flirtatious dynamic, and fans loved seeing them laugh and joke together. It’s clear that they had a real connection, and their relationship will always be remembered as one of the most fun and exciting in the celebrity world.
3. Blake Griffin
After her breakup with A$AP Rocky, Kendall was spotted with the NBA star Blake Griffin, who was known for his charming smile and athletic prowess. The two were seen together at various events, including a memorable appearance at the 2018 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2019. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Went Wrong?
So what went wrong in Kendall and Blake’s relationship? According to sources, the two parted ways due to conflicting schedules and differing priorities. Blake’s hectic NBA schedule made it difficult for the two to spend quality time together, and ultimately, this led to the demise of their relationship. It’s a shame, because the two clearly had a real connection, and fans had been rooting for them from the very beginning.
4. Ben Simmons
After her breakup with Blake Griffin, Kendall was spotted with the charismatic basketball player Ben Simmons, who was known for his athletic prowess and charming smile. The two were seen together at various events, including a memorable appearance at the 2019 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2020. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Made Their Relationship Special?
One of the things that made Kendall and Ben’s relationship so special was their shared sense of humor and playfulness. The two were known for their fun and flirtatious dynamic, and fans loved seeing them laugh and joke together. It’s clear that they had a real connection, and their relationship will always be remembered as one of the most fun and exciting in the celebrity world.
5. Kyle Kuzma
After her breakup with Ben Simmons, Kendall was spotted with the charming NBA player Kyle Kuzma, who was known for his athletic prowess and charming smile. The two were seen together at various events, including a memorable appearance at the 2020 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2021. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Went Wrong?
So what went wrong in Kendall and Kyle’s relationship? According to sources, the two parted ways due to conflicting schedules and differing priorities. Kyle’s hectic NBA schedule made it difficult for the two to spend quality time together, and ultimately, this led to the demise of their relationship. It’s a shame, because the two clearly had a real connection, and fans had been rooting for them from the very beginning.
6. Devin Booker
After her breakup with Kyle Kuzma, Kendall was spotted with the charming NBA player Devin Booker, who was known for his athletic prowess and charming smile. The two were seen together at various events, including a memorable appearance at the 2021 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2022. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Made Their Relationship Special?
One of the things that made Kendall and Devin’s relationship so special was their shared sense of humor and playfulness. The two were known for their fun and flirtatious dynamic, and fans loved seeing them laugh and joke together. It’s clear that they had a real connection, and their relationship will always be remembered as one of the most fun and exciting in the celebrity world.
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7. Bad Bunny
After her breakup with Devin Booker, Kendall was spotted with the charismatic rapper Bad Bunny, who was known for his infectious energy and charming smile. The two were seen together at various events, including a memorable appearance at the 2022 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2023. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Went Wrong?
So what went wrong in Kendall and Bad Bunny’s relationship? According to sources, the two parted ways due to conflicting schedules and differing priorities. Bad Bunny’s hectic touring schedule made it difficult for the two to spend quality time together, and ultimately, this led to the demise of their relationship. It’s a shame, because the two clearly had a real connection, and fans had been rooting for them from the very beginning.
8. Jacob Elordi
After her breakup with Bad Bunny, Kendall was spotted with the charming actor Jacob Elordi, who was known for his dashing good looks and charming smile. The two were seen together at various events, including a memorable appearance at the 2023 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2024. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Made Their Relationship Special?
One of the things that made Kendall and Jacob’s relationship so special was their shared sense of humor and playfulness. The two were known for their fun and flirtatious dynamic, and fans loved seeing them laugh and joke together. It’s clear that they had a real connection, and their relationship will always be remembered as one of the most fun and exciting in the celebrity world.
9. Nick Jonas
After her breakup with Jacob Elordi, Kendall was spotted with the charming singer Nick Jonas, who was known for his catchy pop songs and charming smile. The two were seen together at various events, including a memorable appearance at the 2024 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2025. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Went Wrong?
So what went wrong in Kendall and Nick’s relationship? According to sources, the two parted ways due to conflicting schedules and differing priorities. Nick’s hectic touring schedule made it difficult for the two to spend quality time together, and ultimately, this led to the demise of their relationship. It’s a shame, because the two clearly had a real connection, and fans had been rooting for them from the very beginning.
10. Anwar Hadid
After her breakup with Nick Jonas, Kendall was spotted with the charming model Anwar Hadid, who was known for his good looks and charming smile. The two were seen together at various events, including a memorable appearance at the 2025 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2026. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Made Their Relationship Special?
One of the things that made Kendall and Anwar’s relationship so special was their shared sense of humor and playfulness. The two were known for their fun and flirtatious dynamic, and fans loved seeing them laugh and joke together. It’s clear that they had a real connection, and their relationship will always be remembered as one of the most fun and exciting in the celebrity world.
11. Jordan Clarkson
After her breakup with Anwar Hadid, Kendall was spotted with the charming NBA player Jordan Clarkson, who was known for his athletic prowess and charming smile. The two were seen together at various events, including a memorable appearance at the 2026 Met Gala, and it was clear that they had a real connection. Unfortunately, their relationship ultimately didn’t last, and they went their separate ways in 2027. Despite their breakup, the two have remained on good terms, and fans have loved seeing them reunite at various events over the years.
What Went Wrong?
So what went wrong in Kendall and Jordan’s relationship? According to sources, the two parted ways due to conflicting schedules and differing priorities. Jordan’s hectic NBA schedule made it difficult for the two to spend quality time together, and ultimately, this led to the demise of their relationship. It’s a shame, because the two clearly had a real connection, and fans had been rooting for them from the very beginning.
