Kendall Jenner and Devin Booker: A Complete Relationship Timeline

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What’s old is new again. After dating Bad Bunny for nearly a year, Kendall Jenner has reportedly set her sights back on former boyfriend Devin Booker.

The 28-year-old model and the 27-year-old basketball player were first linked in 2020 before going public with their low-key relationship on February 14, 2021 (you know, Valentine’s Day). Though the relationship appeared solid for a little over a year, breakup rumors waxed and waned the following summer before a more permanent split in November 2022…or so we thought.

Fast-forward to February 2024, and fans were surprised to see Booker in the Kardashian’s Super Bowl suite shortly after Bad Jenner reconciliation rumors surfaced in January. So which romance is really rekindling? Here’s a complete timeline of Kendall Jenner and Devin Booker’s relationship.


March 28, 2018: Kendall Jenner and Devin Booker go on a double date with their (alleged) respective partners at the time. Per photos shared by TMZ, Jenner and NBA player Ben Simmons met up with Booker and Jordyn Woods at Nice Guy in West Hollywood.

May 23, 2019: Jenner and Simmons reportedly split after one year.


April 29, 2020: Rumors start bubbling up about Jenner and Booker when TMZ shares footage of the reality star and the Phoenix Suns player on a road trip amid the coronavirus pandemic. “Kendall and friends have a small social circle amongst the group, who have been following the same social distancing and physical distancing guidelines,” a source tells TMZ. “Devin is a friend and is part of the small group.”

The source continued, “They took a road trip for some much-needed air,” explaining that Jenner and Booker made “a concentrated effort to minimize interactions with other people.”

After two Twitter users disagree about whether basketball players are “passing” her around or vice versa, Jenner herself weighs in, writing, “They act like I’m not in full control of where I throw this cooch.”


February 14: The pair make it official on Valentine’s Day with a picture on Instagram Stories, per Elle.

June 20: Kendall goes on the record about Booker, confirming to Andy Cohen, “He’s my boyfriend,” and opening up about why she keeps their relationship so private: “No offense to my older sisters at all, but I think that Kylie and I specifically have had the opportunity to watch our older sisters go through marriages and relationships and breakups and do them pretty publicly…. I just feel like it’s a private matter and not for anybody else to judge or know.”

October 22: PDA alert! Kendall attends Booker’s game and gives him a kiss (on the cheek, but still) afterward.

Kendall Jenner and Devin Booker on October 22, 2021.

Phoenix Suns v Los Angeles Lakers

Kendall Jenner and Devin Booker on October 22, 2021.
Kevork Djansezian/Getty Images


January 2: Kendall posts a cozy mirror selfie in a dump of her New Year’s weekend. Scroll through!

February 13: The pair have a double date at the Super Bowl with Hailey and Justin Bieber.

March 7: Asked about navigating a life and romance in the spotlight, Booker tells WSJ Magazine, “Honestly, I’m enjoying life to the fullest, and that came off my tongue so easily because it wasn’t always this way, but I feel like I’m in a good place right now.”

Kendall Jenner and Devin Booker are seen arriving at Ristorante Puny in Portofino on May 20, 2022.

Celebrity Sightings In Portofino

Kendall Jenner and Devin Booker are seen arriving at Ristorante Puny in Portofino on May 20, 2022.
Kendall Jenner and Devin Booker arriving for lunch at the Abbey of San Fruttuoso on May 21, 2022.

Celebrity Sightings In Portofino

Kendall Jenner and Devin Booker arriving for lunch at the Abbey of San Fruttuoso on May 21, 2022.

June 23: Just a few weeks after she brought Booker as her plus-one to sister Kourtney Kardashian’s Italian wedding, Entertainment Tonight reports that the pair had split. “Kendall feels like they’re on different paths,” an unnamed source told the publication.

June 27: Despite breakup rumors, Jenner and Booker seem very much on again after photos of the couple leaning against each other began to circulate via TMZ on June 27. Given Jenner is very much hush-hush about her relationships, we took this as her way of saying, “We’re not done yet.”

November 21: Jenner and Booker are fully broken up (again?). Sources close to the couple tell People that they quietly ended the relationship last month due to conflicting schedules and bad timing. They are simply too busy with tequila and basketball. “Both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority,” one of the sources told the outlet.

Another source said, “They have a lot of love and respect for each other and wish only the best.”


February: Around Valentine’s Day, Jenner allegedly makes out with Grammy-winning rapper Bad Bunny at a private club in Los Angeles. Their romance continues to pick up steam (which you can read about here).

December 17: A source tells People that Bad Bunny and Kendall Jenner have split.

Celebrity News

Should we go ahead and call them Bad Jenner?


January 4, 2024: A source tells People that Jenner and Bad Bunny “celebrated New Year together with friends near Barbados.” Despite reconciliation rumors, the insider says they were “not on the same flight,” and are not “back together.”

February 11, 2024: Devin Booker shows up in the same suite as Kendall Jenner at the Super Bowl, according to a photo shared by TMZ. The former couple are not photographed together.

February 23, 2024: TMZ reports that Booker and Jenner are “rekindling” their relationship but are “not even exclusive just yet.” According to their sources, the former couple “have been spending more time together lately” but are “not rushing into things.”

Sources also claim to have spotted Jenner in Dallas around the same time Booker was in town for the Phoenix Suns game against the Dallas Mavericks—interesting!

This post may be updated.

Originally Appeared on Glamour