Exes Kendall Jenner and Devin Booker Reunite During Valentine’s Day Weekend in Aspen

Kendall Jenner and ex Devin Booker enjoyed a cozy meal indoors while together in Aspen, Colorado, over Valentine’s Day weekend.

Kendall Jenner and Devin Booker are getting cozy.

The exes enjoyed some time together in Aspen, Colorado, over Valentine’s Day weekend. As seen in images shared to social media, the pair were bundled up in beanies and snow goggles as they sat side by side in a local bistro.

The outing comes just six months after eagle-eyed fans realized Kendall and Devin—who dated on and off between 2020 and 2022—were in each other’s Instagram Stories at the 2024 Olympics gymnastics final.

And while the appearances could have just been coincidence (after all, the pair were seated on opposite sides of the stadium) it was not the first time the pair just happened to end up in the same place since their breakup. During the 2024 Super Bowl, the model and NBA player ended up in the same VIP suite.

But while the odds are slim that Kendall—who maintains a low profile when it comes to the details of her private life—addresses her current romantic life, there is much to take in for those who are keeping up.

In fact, Devin isn’t the only ex Kendall has been spotted with in recent history. While she and Bad Bunny were connected before they split in 2023, Kendall and the musician have also been seen together on multiple occasions in the time since.

In addition to a reunion at a 2024 Met Gala after-party in May, which precipitated a reunion in Miami that same month, the exes also enjoyed dinner together in Paris in June, though they were joined by Gigi Hadid.

Kendall Jenner, Bad Bunny, Devin BookerGetty Images

Even more recently, Bad Bunny watched from the front row as Kendall walk the runway at the Calvin Klein Collection show Feb. 07 for New York Fashion Week.

With so many sightings of the pair, fans couldn’t help but speculate that Bad Bunny’s latest album, Debí Tirar Más Fotos, was inspired by his time with Kendall—though he was quick to distance himself from such rumors.

“I have written songs inspired by people that people don’t have a f–king clue who they are,” the 30-year-old told TIME last month. “The meaning of the song can vary in many things, like the absence of a person who is no longer with you, or a love. But it can be many other things too, that are no longer there.”

Bad Bunny, Kendall Jenner, New York Fashion Week 2025Jamie McCarthy/Getty Images; Kelly Taub/WWD via Getty Images

In fact, much like Kendall, he’s more than happy to let fans come to their own conclusions rather than divulge anything about his personal life.

“They don’t know how you feel, they don’t know how you live, they don’t know anything, and I really don’t want them to know,” he told Vanity Fair in September 2023. “I’m not really interested in clarifying anything because I have no commitment to clarify anything to anyone.”

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