Kendall Jenner and Devin Booker have stirred speculation yet again. The on-off couple were spotted leaving the same New York City hotel over the weekend.
Jenner, 29, was on her way to a Vogue Fashion Week party. She wore a black-and-white top, long black skirt, and sleek heels.
Booker, 28, kept it casual in all white. He paired the look with a black cap and sunglasses while carrying bags to a waiting SUV.
They exited separately, but the timing still fueled chatter. Days earlier, fans linked Jenner to her other ex, Bad Bunny, at Fashion Week.
The attention has quickly shifted back to Booker, who has been part of Jenner’s romantic life since 2020. Their first public confirmation came on Valentine’s Day 2021 through coordinated Instagram posts.
Kendall Jenner kept it busy this weekend! 🖤 The model hit the Vogue October issue cocktail party at Monsieur on Sunday, grabbed dinner with MGK at Raf’s, and allegedly ex Devin Booker was seen leaving her hotel. 👀 📸: GC Images pic.twitter.com/lo9kT1Bueg
— Page Six (@PageSix) September 15, 2025
By 2022 they had split, with sources citing busy schedules and clashing priorities. Jenner later moved on with Bad Bunny in 2023. That relationship fizzled the following summer when she reportedly wanted “space.”
Soon after, she and Booker were seen together in Miami. The sighting at Surf Club in September 2024 restarted rumors that the NBA star was back in the picture.
Devin Booker and Mikal Bridges linked up in New York recently 🤞🏽♥️
(Via, IG/andfriends) pic.twitter.com/cODtbMNwK8
— CantGuardBook (@CGBBURNER) September 14, 2025
In February 2025, Us Weekly reported they were “very much together” and looking “solid.” One insider said Jenner finds Booker “really funny,” and witnesses claimed they were affectionate at a New York dinner party.
However, by June new reports suggested another breakup. A source claimed they had “gone their separate ways” over a month earlier.
This latest sighting is the first clear sign of a reunion since then. And as usual, the pair have chosen not to confirm or deny anything.
Booker has kept busy on the event circuit. He recently appeared at Reform Casino Night in Atlantic City alongside fellow NBA stars.
Jenner remains firmly in the fashion spotlight. She featured in a Vogue spread with Gigi Hadid and Anna Wintour while also maintaining a front-row presence at runway shows.
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