It wasn’t exactly a double date. On December 17 in Aspen, Colorado, Kendall Jenner met up with pals Hailey and Justin Bieber for dinner at trendy hot spot Catch. But instead of having boyfriend Bad Bunny on her arm, Kendall was flying solo. “She looked a little downcast,” says an eyewitness, “as if something serious had just happened.”

It did. Just days earlier, Kendall, 28, ended her romance with the recording artist (real name: Benito Martínez Ocasio) after less than a year of dating. “They weren’t together long, but they were definitely in love, and Kendall is crushed,” a source exclusively tells In Touch. “She’s had a string of bad romances, and she thought Bad Bunny might be the one.” The two hadn’t been photographed out together since October 29, the morning after their big Halloween bash in LA. Shortly after that photo was taken, Kendall cryptically shared a pic of a sunset with the caption, “what’s meant for me, will simply find me.”

“She saw the writing on the wall,” says the source. “Soon after she posted that, the relationship was officially over. She’s heartbroken.”

What Went Wrong

Up until that point, everything seemed to be going great for the pair. They started dating in February, after the “Dakiti” rapper, 29, relocated to L.A., and were soon inseparable. In the spring, they were spotted horseback riding and cozying up to each other at Coachella. Over the summer, they went on vacation to Idaho, and in September, the two made their front-row debut at Milan Fashion Week to watch Gucci’s spring/summer 2024 fashion show.

“They were as solid as any couple could be,” says the source, “or at least that’s what everyone thought. You never know what goes on behind closed doors. Obviously, there were problems.”

Bad Bunny and Kendall Jenner
Jacopo M. Raule/Getty Images

In the October issue of Vanity Fair, Bad Bunny was cagey about who he was dating, saying he didn’t want to “clarify anything” regarding his private life. “[People] 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 said. But the Puerto Rican superstar did reveal that there was someone in his life he was trying to improve his English for.

“With some people, I speak English — with some specific people,” he said. “With one of them, I couldn’t talk to her before.”

Now they’re not talking at all. “It hurts too much for Kendall to have any contact with him,” says the source. “That said, they both may realize they miss each other and give their romance another chance. It’s not like anyone cheated. So time will tell as to whether they get back together. There’s definitely love there.”

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