Kendall Jenner and Devin Booker Spark Reunion Rumors During Valentine’s Day Weekend in Aspen

Kendall Jenner and Devin Booker were spotted together once again, this time enjoying a cozy getaway in Aspen, Colorado, over Valentine’s Day weekend. The sighting has reignited speculation about their relationship status, as the former couple continues to be seen together in public. 

Kendall Jenner and Devin Booker: An Unexpected Valentine’s Day Reunion

Despite their on-again, off-again relationship from 2020 to 2022, it seems Kendall Jenner and Devin Booker still share a close bond. The duo was seen bundled up in beanies and snow goggles, sitting side by side at a local bistro in Aspen, Colorado, over the romantic holiday weekend.

The images, which quickly went viral on social media, showed the supermodel and NBA star enjoying an intimate meal indoors while embracing the winter charm of Aspen. Fans immediately began speculating—is this just a friendly catch-up, or is there something more brewing between the exes?

Are Kendall Jenner and Devin Booker Back Together?

This Valentine’s Day sighting isn’t the first time Kendall and Devin have been seen in the same place since their split in 2022.

• July 2023 – Fans noticed that both Kendall and Devin shared Instagram Stories from the 2024 Olympics gymnastics final, though they were seated on opposite sides of the stadium.
• February 2024 Super Bowl – The pair unexpectedly ended up in the same VIP suite, once again fueling reunion rumors. 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.
• Multiple Unconfirmed Sightings – Various reports have suggested that the two have maintained a low-key friendship, though neither has publicly addressed their current relationship status.

While it’s possible these encounters were pure coincidence, their frequent sightings have led many to wonder if there’s unfinished business between them.

Kendall Jenner’s Private Love Life: Keeping Fans Guessing

Kendall Jenner, known for keeping her romantic life private, rarely addresses her relationship status publicly.

However, fans have been keeping up with Kendall’s love life—and Devin Booker isn’t the only ex she’s been linked to recently.

Kendall Jenner and Bad Bunny: Rekindling an Old Flame?

Before Kendall’s Aspen reunion with Devin, she was also spotted multiple times with Puerto Rican rapper Bad Bunny, whom she dated in 2023.

The former couple has been seen together on several occasions, leading to speculation about a potential reconciliation.

• May 2024 – The two attended a Met Gala after-party together, which led to an additional reunion in Miami later that month.
• June 2024 – Kendall and Bad Bunny dined together in Paris, alongside fellow supermodel Gigi Hadid.
• February 2024 – The rapper was seen sitting front row as Kendall walked the runway for the Calvin Klein Collection show during New York Fashion Week.

While their interactions appear to be friendly, many believe that Bad Bunny’s latest album, “Debí Tirar Más Fotos,” was inspired by his relationship with Kendall Jenner.

Bad Bunny Breaks His Silence on Kendall Jenner Romance Rumors

Despite the ongoing speculation, Bad Bunny has been adamant about keeping his personal life private.

When asked whether his latest album lyrics referenced his time with Kendall, the “Tití Me Preguntó” singer dismissed the rumors, telling TIME Magazine:

“I have written songs inspired by people that people don’t have a f–king clue who they are. The meaning of a song can vary—sometimes it’s about love, sometimes it’s about loss. But it doesn’t always mean it’s about a particular person.”

In another interview with Vanity Fair, Bad Bunny doubled down on his desire for privacy, stating:

“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. I’m not really interested in clarifying anything because I have no commitment to clarify anything to anyone.”

This statement suggests that he prefers to let fans speculate, rather than confirm or deny his relationship status with Kendall Jenner.

Kendall Jenner’s Love Triangle? Devin Booker vs. Bad Bunny

With Kendall spending time with both exes, it’s hard for fans not to speculate—is she rekindling old flames or just maintaining friendships?

While Devin Booker and Bad Bunny are vastly different in terms of their careers and lifestyles, both have had strong chemistry with Kendall in the past.

Kendall & Devin Booker: A Long History

• The Phoenix Suns star and Kendall began dating in 2020 and had a low-key yet serious relationship for nearly two years.
• They broke up briefly in June 2022, reconciled, but ultimately called it quits later that year.
• Despite the breakup, they have been spotted together on multiple occasions, including their most recent Valentine’s Day weekend in Aspen.

Kendall & Bad Bunny: Passion and Mystery

• Kendall and Bad Bunny first sparked dating rumors in early 2023.
• Their relationship was fast-paced and passionate, with frequent public appearances.
• However, by late 2023, reports suggested that they had quietly split.
• Their continued sightings together in 2024 suggest that they have remained on good terms—or possibly more.

What’s Next for Kendall Jenner’s Love Life?

With both Devin Booker and Bad Bunny in the picture, it remains unclear where Kendall’s romantic future lies.

• Is she rekindling an old romance with Devin Booker?
• Or is she simply staying friendly with her former flames?
• Could she and Bad Bunny be secretly dating again?

Only time will tell. For now, Kendall Jenner seems to be enjoying her freedom, focusing on her career, friendships, and personal growth.

Final Thoughts: Love, Fame, and Keeping the World Guessing

Kendall Jenner’s love life continues to be a topic of fascination, as she navigates relationships under the public eye.

With her Valentine’s Day reunion with Devin Booker and her continued connection with Bad Bunny, one thing is certain—fans will be watching closely to see what happens next.

Whether she’s embracing love, friendship, or simply living her best life, Kendall Jenner proves time and time again that she knows how to keep the world guessing.