A Glimpse into Kendall Jenner's Romantic Journey: Nick Jonas, Harry Styles, Devin Booker, and Beyond

Over the years, Kendall Jenner has been associated with various musicians, athletes, and others. Despite this, she has successfully kept most of her romantic relationships out of the public eye. In a behind-the-scenes video for her Calvin Klein campaign in February 2020, Jenner mentioned, "I think you learn different lessons in every relationship. So I think I’ve learned so many different things from so many different relationships."

Jenner is not one to share much about her personal life, but she has defended herself against negative comments about her dating history. In April 2020, she responded to a troll who made fun of her preference for basketball players after she was seen with Devin Booker.

A social media user captioned a video of three men playfully tossing a little girl in a circle with the words "NBA players passing around Kendall Jenner." Another user replied, "Maybe she's passing them around."

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Jenner then added, "It's as if I don't have complete control over who I date!" Keep scrolling to revisit Jenner's high-profile relationships over the years.

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Kendall Jenner’s Love Life: Nick Jonas, Harry Styles, Devin Booker and More

Kendall Jenner has been linked to musicians, athletes and more over the years — but has managed to keep most of her romances private.

Jenner shared, "I believe that every relationship teaches you something different. I've gained a lot of insights from my various relationships." Despite her usual reluctance to discuss her personal life, Jenner has stood up to critics who have made negative comments about her dating history. In April 2020, she responded to a troll who mocked her penchant for basketball players after being seen with Devin Booker.

The video showed three NBA players playfully tossing a little girl in a circle, with one social media user jokingly captioning it as "NBA players passing around Kendall Jenner," to which another user responded with a playful comment, "Maybe she's passing them around."

Jenner then added, "They behave as if I don't have complete control over my own life!" Check out Jenner's high-profile relationships over the years by scrolling down.

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Harry Styles

Jenner and the former One Direction member were first rumored to be dating in January 2014 after they were seen having dinner together and going skiing at Mammoth Mountain in California. They were then photographed being affectionate and sharing a kiss in December 2015 while on yachts in Anguilla and St. Bart’s. Although their relationship was short-lived, the two have remained close friends: Jenner even showed her support for Styles by attending one of his concerts at The Forum in Inglewood, California in July 2018.

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Nick Jonas

The reality TV star from Keeping Up With the Kardashians and the singer of "Jealous" had a brief romance during the summer of 2015, arranged by her friend Gigi Hadid and his brother Joe Jonas, who were a couple at the time. "Nick was single and interested in dating, and there was an evident mutual attraction," a source informed us at the time. "He definitely finds her attractive."

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Jordan Clarkson

Jenner entered into a relationship with the Cleveland Cavaliers point guard in March 2016. They were seen together at the Coachella Valley Music and Arts Festival the next month and also celebrated the Fourth of July at a party in Malibu. Unfortunately, their romance came to an end shortly afterwards.

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A$AP Rocky

The reality TV personality began socializing with the rapper of "F--kin' Problems" fame in the latter part of July 2016. They made an appearance at a Coachella event in April 2017, and according to an eyewitness who spoke to Us, the pair "were extremely intimate and close." The following month, Jenner and Rocky graced the Met Gala as a couple, displaying affection publicly once again. By September 2017, a source informed Us that although they were not officially together, the two were clearly in a romantic relationship despite their hectic schedules.

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Blake Griffin

In September 2017, Jenner and the Detroit Pistons point guard began seeing each other. A source close to the model confirmed a month later that the pair had officially become a couple. She was frequently seen courtside at his basketball games and even supported him at one of his comedy shows. Jenner expressed her happiness to Vogue in March 2018, saying, “I’m happy. He’s very nice.” Unfortunately, they parted ways later that same month.

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Ben Simmons

The E! personality began dating the Philadelphia 76ers point guard in May 2018, following a short-lived relationship with singer Tinashe. According to an insider who spoke to Us in July, the pair were "dating and exclusive, though not 'official.'" Despite this, they decided to rent a $25,000-a-month home in West Hollywood for the summer and also took a trip to Puerto Vallarta, Mexico, along with her sister Khloé Kardashian and Tristan Thompson. Although their summer fling reportedly ended in September, they reconnected shortly after. An insider revealed to Us in November that "they're still having fun and hooking up." However, the couple ultimately ended their romance again in May 2019.

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Devin Booker

In June 2020, it was confirmed by Us that the reality star and the Phoenix Suns basketball player were casually "hooking up" after rumors of romance started in April during a road trip to Sedona, Arizona. Another source disclosed to Us in October 2020 that they "are still seeing each other, but it's not super serious." Jenner and Booker officially announced their relationship on Instagram on Valentine's Day in February 2021.

The couple seemed to be getting serious when he attended Kourtney Kardashian and Travis Barker's wedding in May 2022. However, the wedding made them reevaluate their relationship and they decided to break up, according to insiders.

A source revealed that the pair are now taking time apart to focus on themselves and determine if they have a future together. They initially broke up in June 2022 but were back together by August 2022.

Us confirmed in November 2022 that the duo had quietly split again "a little over a month" prior, following their reconciliation. At the time, a source noted that the breakup was "amicable."

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Bad Bunny

In February 2023, speculation about Jenner and the Grammy winner dating arose as they attended multiple outings together over the following months.

A source exclusively told Us that while things were not official between Kendall and Bad Bunny, they were seeing each other regularly and getting to know each other better. The source noted that the reality star's feelings for the Puerto Rico native were "starting to grow" after spending more time with him.

According to an insider, the relationship between Kendall and the person she is currently seeing is not extremely serious, but she is interested in him and is willing to see how things develop. Kendall values how he treats her with respect and finds him charming and funny. Despite the relationship being in its early stages, Kendall sees potential in him. The pair were seen openly kissing at an L.A. sushi restaurant in late March, and an eyewitness mentioned that they were very affectionate while dining together.

Jenner and Bad Bunny reportedly split in December 2023 after less than one year of dating.