What’s the deal with Kendall Jenner and Devin Booker’s relationship — for real? The model and basketball player have been off-and-on for about five years now. Things first popped off for the couple in April 2020, when they were photographed on a road trip to Sedona, Arizona.
They didn’t go Instagram-public until February 2021, but when they did, fans were elated by their update. Seeing Kendall support Devin at his basketball games became a common theme. But by June 2022, they were officially dunzo… for the first time.
Now in 2025, they’re back together — but this isn’t their first time reconciling. Will they finally figure out how to navigate their love story this time around?
How Many Times Have Kendall Jenner and Devin Booker Broken Up?
The first reported split between Kendall and Devin was in June 2022, after two plus years together. Entertainment Tonight broke a source’s news — “Kendall feels like they’re on different paths.”
Allegedly, they weren’t on the same page about the futures they saw for themselves. In an interesting twist of fate, they were spotted hanging out together just a few days after that report was published. They even attended a wedding together that July.
It appeared that their relationship was right back on track… until October 2022. That’s when they called it quits again — in a mere three months! According to People, a source said, “[They] both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority… They have a lot of love and respect for each other and wish only the best.”
Fast forward to February 2024, and Kendall and Devin started flirting with reconciliation once again. Coming on the heels of her failed romance with rapper Bad Bunny, reconciliation seemed like a big deal for Kendall and Devin.
Throughout the rest of 2024, rumors circulated about Kendall and Devin’s mysterious relationship status. The tea got especially spicy in September when they were photographed grabbing dinner in Miami.
As of 2025, Kendall and Devin’s relationship is officially back on, according to Us Weekly. A source confirmed, “Kendall thinks Devin is really funny, and they seem very solid right now.” They added that the couple is “very much together.”
Off-and-on relationships aren’t always the most reliable, but if Kendall and Devin are serious about making this work, we’re certain they’ll make it happen.
But Who Else Has Kendall Jenner Dated?
As previously mentioned, Kendall dated Bad Bunny during one of her off-seasons from Devin. Although the “Monaco” rapper isn’t the only person who stole Kendall’s heart.
Her relationship history includes NBA all-star Ben Simmons, whom she dated from July 2018 until May 2019. Dating basketball players seems to be the norm for Kendall who also dated Blake Griffin from August 2017 until February 2018.
Speculation about Kendall dating A$AP Rocky from July 2016 until early 2017 also made the rounds. And then she was linked to Jordan Clarkson in 2016 after dating Harry Styles in 2015.
Kendall’s star-studded dating history is intriguing, but her fans are super curious about what’s next for her and Devin. Are wedding bells in the future?
Are Kendall Jenner and Devin Booker Headed Toward Marriage?
If you’re curious to know if Kendall will ever take the next step by marrying Devin, we’ve got a bit of an answer. Her mother, Kris Jenner, spoke on the topic candidly with People.
When asked if she or her daughters have any wedding plans, she quickly shut that down, saying, “All of us are having fun, and we have no marriage plans — yet.”
In 2023, Kendall herself spoke about the possibility of settling down on an episode of The Kardashians. When asked about how many kids she hopes to have someday, she said, “Three max. I’m cool with two though. I just want my kid to for sure have a sibling.”
Is it possible she’ll be taking these major steps with Devin by her side? Fans of the Kardashian-Jenner clan will undoubtedly find out more about that in due time.