Kendall Jenner and former boyfriend Devin Booker were seen leaving the same New York City hotel over the weekend, prompting renewed speculation that the pair may be rekindling their on-again, off-again relationship.
The 29-year-old model and the 28-year-old Phoenix Suns guard departed the hotel separately as Fashion Week activity swelled in the city. Jenner left en route to a Vogue-hosted party, wearing a long black skirt and a black-and-white top with pointy-toe black heels and an updo hairstyle. Booker exited later in an all-white outfit with a black hat and sunglasses, carrying two black bags and a black garment before heading to a waiting SUV.
The sightings were reported by the Daily Mail, which noted the separate departures and the pair's recent social activity in the city. Neither Jenner nor Booker has publicly confirmed their current relationship status. Both have remained active on social media, sharing professional and social posts in recent weeks; Booker recently reposted a photo from an event in Atlantic City, while Jenner reshared a Vogue post that included Gigi Hadid and Anna Wintour.
The pair first dated from 2020 to 2022. Their relationship has since been punctuated by other reported romances and periodic reunions, according to multiple entertainment outlets. Jenner was linked to music artist Bad Bunny in early 2023; reports in 2024 indicated she and Bad Bunny had cooled off after summer travels in Europe. In early September 2024, Jenner and Booker were seen together at Miami’s Surf Club, an appearance that media outlets said signaled they were spending time together again.
Since then, accounts of their private lives have varied. In May 2025, Booker was photographed with stylist Molly Murphy at the Stagecoach music festival. In February 2025, Us Weekly reported that an insider said Jenner and Booker were “very much together,” adding that Jenner found Booker “really funny” and that they appeared “very solid” at the time. The same report quoted a source saying the pair had been affectionate at a recent dinner with friends but preferred to keep their relationship private.
Representatives for Jenner and Booker did not immediately respond to requests for comment. The latest hotel sightings come amid New York Fashion Week, a period when celebrities' public appearances and after-parties often generate renewed attention to personal relationships.
Public interest in Jenner’s private life has been sustained by her high-profile career as a model and her visibility within fashion and entertainment circles. Booker, a professional athlete with the Phoenix Suns, has also attracted media attention for his personal life and appearances at social events. For now, available reports show only that the two were seen leaving the same hotel; neither party has issued a statement confirming a reunion.
Reporting on celebrity relationships often relies on sightings, social media activity and comments from unnamed sources; outlets that cited those elements in recent coverage include Daily Mail and Us Weekly.