Entertainment And News

The Harsh Reason Kendall Jenner's Relationships Have Ended — Her Romance With Bad Bunny May Be Doomed Already

Photo: Andrea Raffin / Shutterstock, Instagram & mykola-lytvynenko via CanvaPro
Bad Bunny, Ben Simmons, Kendall Jenner, Devin Booker

Kendall Jenner's romance with Bad Bunny may be already set up to fail if her past relationships are anything to go by.

The rumored new couple have been getting close in recent weeks with dinner dates and kisses under the glare of paparazzi and fans are divided about whether they ship the duo or want both parties for themselves.

The 27-year-old model's relationship with the 28-year-old Puerto Rican singer has come off the back of Jenner's many high-profile romances. She dated Phoenix Suns guard Devin Booker for two years until their breakup in October 2022. Before Booker, Jenner started dating another NBA star, Ben Simmons, in May 2018 and dated on and off for two years.

But these breakups have one key detail in common that may spell trouble for Jenner and Bad Bunny, whose real name is Benito Antonio Martínez Ocasio.

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Why did Kendall Jenner's previous relationships end?

According to sources who spoke on Jenner's previous breakups, the model and her sport star exes struggled to make time for one another due to their busy schedules — a problem her new rapper beau might also battle given his hectic career.



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In November 2022, a source told People Magazine that Jenner and her most recent ex, Booker, had broken up in October because they “both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority.”

While Booker, 26, traveled with the NBA, Jenner spent her time focused on her modeling career and 818 Tequila brand, which was founded in 2021. Their breakup was reported to be “mutual.” It was a split that “just came down to timing.”

There was apparently no bad blood between the exes, as they had “a lot of love and respect for each other,” but couldn’t make their relationship work due to distance and timing.

Before she dated Booker, Jenner's relationship with Simmons also ended due to conflicting schedules.

While the two were reportedly “on fine terms and have been in touch,” since their split, an E! News insider stated that the distance between them was “getting to be a lot.”

"Kendall knew she had several out-of-the-country trips coming up and thought it would be best if they took some space,” stated the source. “It's been hard for them with the time differences and both of their schedules.”

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While distance can make the heart grow fonder, Jenner likely knows that a strong relationship needs quality time.

It’s very valuable for individuals to have their own goals within a relationship and to take time for themselves, whether to focus on their careers or other activities. But it’s also important for couples who want to stay together to focus on each other.

In January, Sidhharrth S. Kumaar who has ten years of experience counseling couples and working with people seeking to strengthen their relationships, told YourTango that quality time is a vital part of creating and maintaining lasting love. 

"Having a successful relationship requires effort, dedication, and the ability to grow and develop alongside one another," he told us. "There is no substitute for face-to-face communication” in relationships, advising couples to “do your best to schedule frequent quality time together.”

“No matter how hectic your schedule is, make time every day to disconnect from technology, clear your mind, and reconnect with your significant other.”

Both Jenner and Bad Bunny have flourishing careers, and lives that are independent of one another. However, there may be good news for the future of their relationship.

Bad Bunny is taking a break this year, right as his romance with Jenner is picking up.

He’s stated to Billboard that he’s planning to take a break from any major commitments in 2023.

“2023 is for me, for my physical health, my emotional health to breathe, enjoy my achievements,” Bad Bunny explained. As Jenner and Bad Bunny seemingly embark on a new romance with one another, they’d do well to keep in mind that strong, lasting couples need to spend quality time together for their relationship to flourish.

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Alexandra Blogier is a writer on YourTango's news and entertainment team. She covers celebrity gossip, pop culture analysis and all things to do with the entertainment industry.