Kendall Jenner'S Love Diary: A Journey Through Her Star-Studded Romances

Kendall's Private Approach to Love

Kendall Jenner, unlike her famous family, prefers to keep her romantic endeavors under wraps. In a candid 2019 chat with Vogue Australia, she expressed her desire to maintain a sense of mystery in her love life. "For me, a lot of things are very special and very sacred, like my friends and relationships," she shared. "I personally think that bringing things into the public makes everything so much messier."

As of January 2026, the supermodel remains single, choosing self-prioritization over relationships. On the "In Your Dreams With Owen Thiele" podcast, she revealed, "When I turned 29, I was like, I really want to put myself first right now. And so that’s where I’m at."

Harry Styles: A Not-So-Secret Fling

Kendall's flirty history with Harry Styles kicked off in 2013, shortly after his split with Taylor Swift. Despite denying romantic ties, their on-and-off connection was undeniable. "There has been a lot of flirting, touching and snuggling going on," a source told People during their 2016 St. Barts getaway.

In 2019, Jenner playfully grilled Styles about songs possibly inspired by her during a "Late Late Show" segment, to which Styles humorously opted for silence over spilling the beans.

From Jonas to Clarkson: Brief Encounters

Rumors swirled in 2015 about Kendall's casual fling with Nick Jonas, set up by mutual friends. However, Nick quickly shot down dating speculations, emphasizing their platonic bond.

In 2016, Jenner was spotted cozying up with NBA star Jordan Clarkson, but their relationship never quite reached the serious stage.

A$AP Rocky and Blake Griffin: More Than Just Friends?

Jenner's rumored romance with A$AP Rocky in 2016–2017 was marked by public outings and intimate moments. Yet, their busy schedules eventually led to a drift.

Soon after, Kendall was linked to Blake Griffin in 2017. Their relationship seemed promising, but distance played a part in their eventual split.

Ben Simmons and Devin Booker: Serious Courtships

Jenner's time with NBA star Ben Simmons in 2018–2019 became public when she confirmed their relationship on "The Ellen DeGeneres Show." However, their romance fizzled out by mid-2019.

Devin Booker entered the scene in 2020, and the couple enjoyed a promising two-year relationship. Despite a brief 2022 split, they rekindled their romance in 2025, only for it to end once more.

Bad Bunny: A Modern Love Story

Kendall's 2023–2024 fling with Bad Bunny had its ups and downs, with the pair sharing a flirty dynamic and mutual friends. Despite a split in December 2023, they reunited briefly in 2024 before parting ways again by September.

Kendall Jenner's dating history is a testament to her preference for privacy amid a life lived in the public eye. Her relationships, though often with fellow celebrities, reflect her desire to navigate love on her own terms.