Devin Booker’s Dating History: All About His Romance With Kendall Jenner & Past Loves

NBA Player Devin Booker is romantically linked to Kendall Jenner once again following their on-and-off past. Take a look back at his full dating history.

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Image Credit: John Angelillo/UPI/Shutterstock

Although NBA player Devin Booker may be a beast in the court, his love life has been a little more up and down in the past. He has been involved with two famous models since 2018 and his relationships have always been in the spotlight. His most recent on-and-off romance with Kendall Jenner reportedly reignited less than two years after breaking up in 2022.

Keep reading to find out more about his romantic endeavors here.

Jordyn Woods

Jordyn Woods
Jordyn Woods (Chelsea Lauren/Shutterstock)

Devin and Jordyn Woods, who was Kylie Jenner‘s best friend at the time, were rumored to be linked in May 2018, per TMZ. This was after they were spotted on a double date with Kendall Jenner and her then boyfriend, NBA player Ben Simmons. Although the relationship was never officially confirmed, a source told MTO News in July 2018 that Devin and Jordyn were in love. “I’m not going to say that they’re getting married because it’s still early, but they’re definitely a couple,” the insider stated.

A scandal broke out in February 2019 when Khloe Kardashian‘s then boyfriend Tristan Thompson reportedly kissed Jordyn. However, Jordyn and Devin were supposedly no longer together by the time this occurred, according to US Weekly

Kendall Jenner

Kendall Jenner and Devin Booker
Kendall Jenner and Devin Booker (John Angelillo/UPI/Shutterstock)

Devin and Kendall were first spotted together on a road trip in April of 2020. Since then, they were seen on a plethora of outings together. Although a source originally told PEOPLE that the pair were just looking for a “fun hookup,” they went Instagram official on Valentine’s Day in 2021, with their first year anniversary being in June 2021. Kendall talked about Devin on The Tonight Show in September 2021, gushing over how close he was with her family. In May 2022, the pair attended Kourtney Kardashian’s wedding in Italy, and the event reportedly was a major reason behind their breakup a month later.

“Kendall broke up with him because she didn’t think he was taking the relationship as seriously as she was. Kendall felt like it was a really big deal to bring him with her to Kourtney’s wedding and she thought it would be super romantic. But it didn’t turn out like that at all, and he couldn’t have seemed more disconnected from the love and romantic aspect of it” an EXCLUSIVE SOURCE told Hollywood Life.

“Even though she’s not at a place right now where she wants to get married and have kids, it’s also something she knows she eventually wants,” they added. “Devin was clearly not on the same page and explained how there’s much more he wants to do in life. She had a lightbulb moment and is coming to terms with the fact that even though they had a great run, ultimately it’s not what she wants.” The insider also stated that Devin was devastated by the split.

However, Kendall and Devin sparked reconciliation rumors in late June 2022 when they were spotted together in Malibu. Apparently, Devin had been making attempts to win the supermodel back, even filling her house with flowers. “It seems like her breaking up with him was a real wake-up call. She didn’t do it to play games or mess with his head, but it definitely got his attention,” an EXCLUSIVE SOURCE told Hollywood Life. A second insider even stated that they suspect that Devin is going to propose to Kendall in order to not lose her once and for all.

Devin and Kendall kept their reconciliation under wraps more than when they were together before that and their romance would make headlines once in a while. On November 21, 2022, it was reported that the lovebirds had called it quits “quietly” in October 2022. “Both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority,” a source told PEOPLE. “They have a lot of love and respect for each other and wish only the best.”

In February 2024, though, Kendall and Devin were “rekindling their relationship,” according to TMZ. However, the outlet reported that the duo was “taking things slow — and they’re not even exclusive just yet.”