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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.

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

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June 23: Just a few weeks after bringing 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 told 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.”

2023

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.

2024

January 4, 2024: A source tells People that the 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.


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