Kendall Jenner, Devin Booker Might Be Back Together With Valentine’s Weekend Aspen Trip

All eyes are on the exes as they’re spotted together during Valentine’s Day weekend.

Kendall Jenner and Devin Booker / NINO/GC Images/Getty Images

Friendly exes or getting back together? That’s the question on fans’ minds as a photo of Kendall Jenner and Devin Booker hanging out in Aspen, Colo. was released.

The supermodel, 29, and Phoenix Suns player, 28, were in a committed relationship from 2020 to 2022, and while reports of reconciliation came out about a year ago, nothing has been confirmed since then. They say a picture is worth a thousand words, however, and we’ve got a new one to investigate after the pair was photographed sitting at a table at a restaurant side by side. They were joined by others for their outing, which saw them decked out in cold weather attire perfect for skiing or snowboarding.

Celebrity gossip site Deuxmoi shared the exclusive, reporting they were seen at the Cloud 9 Alpine Bistro over the past weekend, which just so happened to mark Valentine’s Day weekend.

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Jenner and Booker began sparking romance rumors five years ago when spending time together during the pandemic. Going on a road trip together in Arizona, fans were on high alert for their potential romance, especially when the Kardashians star clapped back at a nasty tweet with a hilarious—and telling—message.

Though they remained pretty private throughout their two-year relationship, Jenner and Booker shared sweet signs of support for each other on social media and, occasionally, spoke about one another in interviews.

“He loves them,” Jenner said of Booker’s relationship with her young nieces and nephews during an appearance on The Tonight Show in 2021. “Him and [Kylie Jenner’s daughter] Stormi have an amazing relationship. She has the biggest crush on him, and I’m jealous sometimes. I’m like, ‘Stop. Can you guys not?’”

After some reported on and off, Jenner and Booker called it quits for good—at least that’s what it seemed—in late 2022. In the years since, the 818 Tequila founder moved on to Grammy Award-winning artist Bad Bunny, who she dated on and off through 2023 and 2024.

Jenner’s love life is no doubt juicy for fans to keep up with, though we doubt she’ll address her latest trip with her ex. Though she’s documented previous trips to Aspen on her Instagram grid—even one as recent as last month—she has not shared any photos from this one on her social media. As discovered by Sportskeeda, however, Booker’s brother Davon Wade shared snowboarding flicks from Aspen, celebrating his 32nd birthday. It’s not a stretch to assume Jenner tagged along for a family trip.