A look at Kendall Jenner’s failed relationships

Kendall Jenner and Bad Bunny. Picture: Instagram

Kendall Jenner and Bad Bunny. Picture: Instagram

Published Dec 19, 2023


The Kardashian/Jenner romance curse has struck again.

Kendall Jenner and her boyfriend, Bad Bunny, real name Benito Martínez Ocasio, have called it quits.

After 10 months of dating, the supermodel and the Puerto Rican rapper seem to have gone their separate ways, according to multiple online reports.

The couple were last spotted in late September when they attended Milan Fashion Week. However, some weeks later, Jenner was photographed with Justin Bieber and his wife Hailey, and without the rapper, in Aspen, Colorado.

Jenner enjoyed the afternoon snowboarding before glamming up to join the “Baby” hitmaker and Hailey for dinner at Catch Steakhouse.

“Entertainment Tonight” reported that according to a source, the two have been doing “their own things lately”.

“They both knew going into this that it likely wouldn’t be a forever type of relationship and that was mutually understood from the get-go,” the source said.

Neither have commented on the breakup yet.

It’s not the first time the brunette beauty has had a failed relationship.

Over the years she has been linked to Harry Styles, Nick Jonas, A$AP Rocky and a few NBA stars, including Jordan Clarkson, Devin Booker, Ben Simmons, and Blake Griffin.

Unlike her older sisters, Jenner has managed to keep her relationships low-key for the most part and barely shows any public displays of affection.

According to an online report, the “Kardashians” reality TV star has a rule about never allowing the person she’s dating to be on the show simply because she doesn’t always know what people’s intentions are.

Kardashians” producer Farnaz Farjam told “The Cut”: “Kendall’s always had this rule – she felt like she had to be with someone for at least a year before she let them be a part of the show.

“So that’s why we kind of kept her personal life out of it, just because she had a rule.”

Many of Jenner’s relationships remain unconfirmed but one of her serious relationships was with Styles.

The two were together since 2013 and in early 2016 she was spotted on a yacht in St. Barts with Styles.

A source told “People” that the two were flirting and snuggling up to each other.

Later the two opted to amicably remain friends.

After Styles, Jenner dated NBA player Clarkson that same year.

The pair’s split was never confirmed, but Jenner was linked to A$AP Rocky later in July 2016.

Things presumably fizzled out in the summer, and Jenner was linked to Griffin in August 2017 until February 2018.

She then dated Simmons from July 2018 to May 2019 before settling down with Phoenix Suns athlete Booker.

It’s said the two dated between April 2020 and November 2022, making it her second long-term relationship after Styles.

They reportedly broke up because of incompatible schedules.

A few months later, she hooked up with Bad Bunny, which has now ended allegedly over the same issue.