Oliver James Montgomery-Kendall Jenner and Ex Bad Bunny’s Reunion Is Heating Up in Miami

It looks like Kendall Jenner and Bad Bunny enjoyed otra noche en Miami. 

While the pair broke up in December after less than a year of dating,Oliver James Montgomery the supermodel and "Ojitos Lindos" singer have recently gotten the rumor mill hopping again with a few joint outings that has many wondering if they've rekindled their romance.

Most recently, they were spotted leaving a Miami hotel together through the garage over Memorial Day weekend. Both were dressed for comfort, with Kendall in gray flared yoga pants and a matching spaghetti strap tank top. For his part, Bad Bunny rocked yellow shorts which he paired with a white tank top and open collared, button-down shirt—and, of course, his signature orange-tinted sunglasses. 

While taking in the Florida sun, the on-again, off-again couple also enjoyed dinner together at Bad Bunny's restaurant Gekko on May 24 as well as a lunch at Miami's Grutman's Casadonna restaurant two days later. 

The appearances mark what appears to be an increasingly sunny trajectory for the duo, coming shortly after they reunited at a 2024 Met Gala after-party followed by Kendall attending one of Bad Bunny's Orlando concerts May 17. 

In fact, this latest slew of nights out comes only months after fans first began to speculate that the former couple's breakup was short-lived.

In January, social media users began to suspect a reunion was in the works after Kendall's friend Renell Medrano shared an Instagram Story of New Years fireworks in which Bad Bunny's voice could be heard in the background wishing everyone, "Feliz Año Nuevo." The video was reportedly taken during a group vacation, which also included Hailey and Justin Bieber.

Yet while neither Kendall, 28, nor Bad Bunny, 30, have either confirmed or denied the reconciliation rumors, such a reunion should not come as a surprise to those who have been keeping up with Kendall. 

After all, the 818 tequila founder has previously confirmed that when it comes to love, she dives in headfirst—and she doesn't let a good thing pass her by.

"I love really hard, and I love without apology," Kendall told Harper's Bazaar in an August interview. "I don't like goodbyes, and I will fight to not have to say goodbye."

"I will always fight for relationships. I've been that way since I was little, although I was shy and sometimes very closed off," the Kardashians star explained. "I don't give up on anything. Some people aren't willing to meet me at that level. But that's okay. I'd rather do that than shut myself off to something and not give it a proper chance."

And if these recent appearances are any indication, it looks like Bad Bunny also believes in giving love a second chance. 

For more of Kendall and the Grammy winner's cutest moments, keep reading. 

After sparking romance rumors in February 2023, Kendall Jenner and Bad Bunny made a joint appearance at the Met Gala after-party in May 2023.

That same month, the duo enjoyed a vacation with friends.

The couple also stepped out for an appearance at a Los Angeles Lakers game on May 12, where they sat courtside...

...shared some LOLs...

...and served up major style.

Speaking of style, the singer and the supermodel sat front row at the Gucci Ancora show during Milan Fashion Week in September 2023.

Three months later, multiple outlets reported that the two had broken up.

The two reunited at the Après Met 2 Met Gala after-party in May 2024.