The supermodel and the NBA star were first spotted together in April 2020, but they actually met years earlier when Jenner was still dating ex-boyfriend Ben Simmons. In May 2018, the Keeping Up With the Kardashians alum and the Australia native joined Booker and Jordyn Woods for a double date. The Masked Singer alum was then BFFs with the 818 Tequila founder’s younger sister, Kylie Jenner.
Two months after Kendall and the Phoenix Suns guard took a road trip to Arizona, Us Weekly confirmed that the duo were dating. “They’re hooking up, but they’re not serious,” an insider revealed at the time. “She’s talking to a couple different guys. She has so many men after her it’s crazy.”
The romance seemed to get a bit more serious later that year, however, when Booker made an appearance at Kendall’s 25th birthday party. The reality star shared an Instagram photo of herself and the athlete cuddled up at the October 2020 event.
In February 2021, the couple made their relationship Instagram official when Kendall shared a photo of herself snuggling with Booker on her kitchen counter. “They were tired of the media frenzy and were ready to confirm their romance,” a source told Us at the time. “They care about one another immensely.”
Though the couple began dating before KUWTK ended for good in June 2021, the Michigan native never made an appearance on the show — and that’s how the cover girl wanted it.
“Kendall’s always had this rule — she just felt like she had to be with someone for at least a year before she lets them be a part of the show, because she doesn’t always know what people’s intentions are,” KUWTK executive producer Farnaz Farjam told Bravo TV’s “The Daily Dish” podcast in June 2021. “So that’s why we kind of kept her personal life out of it, just because she had a rule.”
Though Kendall and her beau had made it past the one-year mark by the time the Kardashian-Jenner family started filming their new reality show, she still planned to take it slow with the Olympic gold medalist.
“Kendall is taking a slower approach to relationships, as she always had a different approach from her sisters,” an insider exclusively told Us in March 2022. “Their relationship works very well because they have that work [and] life balance.”
The twosome called it quits in June 2022, per insiders, but are “still super amicable and supportive of each other.” One source added that they could reconcile as they “figure out if a future together is what’s meant to be”
— which is exactly what happened after weeks apart. The two reunited by the following August.
“They spent some time apart but are back to a good place and are really happy with each other,” an insider told Us at the time. “They’re spending a lot of time together and are looking forward to what the future holds for them as a couple.”
Keep scrolling for a look back at Jenner and Booker’s sweetest quotes about each other.