The Fascinating Love Life of Kendall Jenner: A Complete Timeline

Kendall Jenner, a global icon and one of the most famous members of the Kardashian-Jenner family, has always been the center of attention—not only for her modeling success and glamorous lifestyle but also for her intriguing love life. Despite her preference for privacy, her relationships with celebrities and high-profile personalities have kept fans and media engaged.

From hinted at flings to well-known relationships, this piece looks at Kendall Jenner’s dating past to show how interesting her love life has been.

 

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Early Rumors and Teenage Flings

Before she became well-known, Kendall followed the usual teenage flirtation and dating. People who were young at the time were interested in Kendall as a model, but not much is known about her early love life.

The Harry Styles Era: 2013–2016

2013 saw Kendall first connected to former One Direction member and British pop sensation Harry Styles. Following his breakup from Taylor Swift, Harry and Kendall were seen together in Los Angeles, fuelling dating rumours.

Their relationship stayed unclear, although they were seen vacationing together over the 2015 Christmas season and even spending New Year’s together. People magazine reported in September that they were no longer together, but they were pictured many times in 2016.

NBA Stars and Hollywood Flings: 2016 – 2018

Jordan Clarkson: 2016

It’s officially casual: Kendall Jenner and Jordan Clarkson are dating. https://t.co/Edrt0eT2hL pic.twitter.com/V8VO7Y4okZ

— E! News (@enews) July 6, 2016

Kendall first started seeing NBA player Jordan Clarkson early January 2016. Along with those get-togethers, they went to Drake’s party after the American Music Awards and Kendall’s 21st birthday celebration. Their romance, though, was fleeting; it broke apart later that same year.

A$AP Rocky: 2016 – 2017

After they met in Paris, Kendall started documenting her courtship of rapper A$AP Rocky in June 2016. Their relationship seemed genuine since Kendall was there for him at events like Coachella and Art Basel Miami. Though they split up at last, they went to the 2017 Met Gala together.

Kendall Jenner and A$AP Rocky Are Officially Dating https://t.co/QJE0acYeb3 pic.twitter.com/PtpHyNgx9z

— Cosmopolitan (@Cosmopolitan) August 10, 2016

Blake Griffin: 2017 – 2018

Kendall then connected with NBA player Blake Griffin. She regularly showed up in the summer of 2017 at his first activities. Though they appeared to be, Kendall wouldn’t reveal whether they were dating. By March 2018 they were no longer together.

She’s not a cheerleader anymore, but that didn’t stop Kendall Jenner from supporting Blake Griffin courtside. https://t.co/0slsAiMM7f pic.twitter.com/YwA64pfp7b

— E! News (@enews) November 5, 2017

Ben Simmons’s relationship: 2018 – 2019

May 2018 saw Kendall beginning a relationship with NBA player Ben Simmons. She finally spoke about the relationship on The Ellen DeGeneres Show in early 2019 after silence on it for some time. Sadly, they split shortly after becoming public, and Kendall claimed their hectic schedules had a role.

Kendall Jenner is courtside cheering on Ben Simmons 👏 pic.twitter.com/uJ8v9Z8esC

— NBA on ESPN (@ESPNNBA) November 24, 2018

The Devin Booker Chapter: 2020 – 2023

In April 2020 Kendall started seeing NBA player Devin Booker. Their relationship developed and became among her most public and oldest one. Kendall formally announced their romance on Valentine’s Day 2021 on Instagram, and in June of that year they celebrated their one anniversary.

They’re officially no longer on a break. Kendall Jenner and Devin Booker are back together. pic.twitter.com/UhfQEvciqV

— E! News (@enews) July 19, 2022

Kendall went to several of Devin’s games, and the pair posted peeks of their trips. Though they had a close relationship, they briefly broke up in June 2022 but got back together one month later. But by November 2022 they resolved to split ways. Resurfaced rumours of a reconciliation between Kendall and Devin in 2024 had fans on edge.

The Bad Bunny Encounter: 2023 – Present

The surprising but interesting combination of Kendall and Latin music sensation Bad Bunny was First sighted together in Beverly Hills in February 2023, they were regularly seen thereafter attending events including Coachella, the Met Gala, even a Lakers game.

Bad Bunny shares video with Kendall Jenner on his Instagram story:

“Mami be careful” pic.twitter.com/XuDEaZjixE

— Pop Base (@PopBase) August 27, 2023

Though apparently splitting in December, the two spent New Year’s Eve together and were back together in May 2024. After attending the Met Gala afterparty and seeing on other occasions, Kendall was once more connected to Devin Booker in September 2024, so indicating a possible breakup of her romance with Bad Bunny.

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Conclusion

From celebrities to sportsmen to cultural icons, Kendall Jenner has dated many fascinating people. From her reported flings with teenagers to her recorded romances with celebrities like Harry Styles, Devin Booker, and Bad Bunny, Kendall’s love life has been an interesting component of her public image.

Though no one knows what her love future has yet, people are still enthralled with her enigmatic beauty and incredible talents and eager to see who she meets next on her incredible trip.